I love interviewing people and unfortunately have not had the chance to interview a candidate for the last few years. Specifically I like meeting new people and learning about them. Some folks recently asked me about what my interview process is so I dug up my notes and polished them.

In this article I’ll start by discussing how I begin an interview and then the kind of questions I use for specific positions. I’ll also go into detail of why I ask the question and what I’m looking for.

In general I prefer what’s known as “behavioral” interview questions. By asking people about their experiences you get a sense for how they have handled similar issues in the past. It’s harder, but not impossible, to “lie” for behavioral questions.

Keep in mind, interviews are a two way street. You want to show candidates that you are somebody they might want to work with and that there is value in being at your company. While the hiring market has ups-and-downs, you don’t want to leave an interviewee with a bad perception about you or the company even if you don’t think the person should be hired.

Often interviewers are advised to do the entire interview even if they know early on that the candidate isn’t a fit and the interviewer will recommend against hiring. In part, this advice is to prevent a candidate from feeling they are being discriminated against or give a candidate a bad experience that they share on social media. If you are the hiring manager, or somebody that has and will veto their candidacy I think it can be valuable, especially for people new to the job market, to tell them why they aren’t a fit and where instead they should consider interviewing. For example, I’ve had several candidates who interviewed at a startup that clearly would prefer to work in a more established/stable company and I’ve advised them accordingly.

Interview Prep

Take time to pre-read the candidate’s resume. The resume can be a great source of behaviour questions. They should be able to talk in detail about everything on it so you can potentially pick a couple things to ask about that are relevant to the job. You might want to ask the other interviewers what they will be asking to limit overlap.

You should read a candidate’s LinkedIn. You may also want to do an internet search for them and check their GitHub.

Have a document or paper with your questions. I’ve totally blanked on my questions. Write down notes on what they say vs “pass”/ “fail”. Don’t write anything you’d be embarrassed for the candidate to see. The details of the answer can help qualify your rating.

Remember that you are human. If somebody spilled coffee on you and your kid just got an “F” in math don’t take it out on the candidate. Research shows that interviewers who are in bad moods give more negative feedback about candidates. This is why your notes can be critical in helping you compare candidates more objectively.

Sometimes you end up having less time than planned for interviews. Feel empowered to tell a candidate to be more concise. If you are running low on time make sure to get to the highest priority questions and still give them time to ask questions.

Opening

• Intros - State pronouns (don’t ask for them), title, when joined, etc.

  • This may seem obvious, but it’s important to start with introductions. Candidates are nervous and starting with easy conversation will reduce the nervousness. Start by introducing yourself and sharing your pronouns. Do not ask the candidate for their pronouns because they may not feel safe to share, may be in the closet, and may be insulted by the question. Tell them your title at the company and when you joined. Give them an opportunity to introduce themself. If they state their pronouns make sure you write them down.

• Anything they need? - Water, bio break, etc.

  • Make sure they are comfortable. Maybe they just got into the office from an intense weather day. Often interviews are back-to-back and the candidate might need a bio break. Ask them if they need a break, water, or anything else! Do not hold it against them if this reduces your interview time.

• Discuss Group and Role

  • Don’t assume they understand the details of the group or role. Sometimes job postings are very generic. A candidate might be interviewing for several different positions at once and misremember getting the details jumbled. Give them your insider perspective of what the group is, what the culture is, and what they would be expected to do if hired.

For All

• Career Goals

  • This is a critical question, which is why I list if first. As an interviewer, especially a hiring manager, I want to make sure the candidate’s longterm goals can align with the goals of the team and company. If a candidate has the goal to be a phlebotomist and I’m hiring a software engineer they probably won’t be happy if I hire them. I won’t have any assignments that lead them to their phlebotomy dreams.

• Interest in Company

  • This tells you if they’ve done their homework on the company. I don’t consider this a pass/fail, it’s possibly they blanked on the details about the company. This also gives you a chance to clarify what the company does.

• Tell me about your Worst Boss. I don’t want to know who they are, but what about them made it difficult for you to work for. It doesn’t have to be a boss, it could be a commander, captain, coach, professor, etc.

  • This is probably more useful for a hiring manager to ask. The intent here is to hear a story relating to what they disliked with a past manager. If, for example, they disliked being macromanaged and you consider yourself a macromanager maybe this won’t be a good fit. Asking them this also can show you as a leader are open to feedback from employees.

• Tell me about your Best Boss

  • Similar to the prior question, this helps tell a hiring manager if they would work well with the candidate. If you can’t hope to be in the same ballpark as what they are looking for in a leader this might not work out.

• What have you learned recently?

  • If you have a job where people have to continually learn you might prefer to hire somebody who has a passion for learning. I think it’s important to be open to the learning they list being unrelated to the work.

• What motivates you to come into work every day?

  • This helps you get a sense for a person’s intrinsic motivation. Can you provide an environment where this person will feel motivated to work?

• How do you rely on others to make you better?

  • I ask this to get a sense of a person’s ability to be a part of a team and to gauge their humility.

• Who inspires you and why?

  • This can be an alternative to the best boss/worst boss. It helps you determine if the candidate can be inspired by the team.

• Questions for me?

  • This is a critical question. Interviews are a give and take. It is frustrating to be a candidate and not be able to ask any questions. These questions also can give you further insight into what the candidate is looking for and if you can provide it. This can also show you they’ve thought about the role. Sometimes the questions will reflect how they’ve been burned at prior companies and if they would similarly be burned at your company. It’s okay if they say they have no questions. They may have already asked all their questions, they may have forgotten their questions, or they may be uncomfortable asking their questions to you specifically (which is okay).

• Still Interested?

  • If in the interview they’ve realized they don’t want the job this will save everybody time to know now. Thank them for whatever response they give you. If they aren’t interested make sure the recruiting team knows directly after you finish meeting with the candidate.

Customer Success Engineer Questions

• An example of improving a customer relationship?

  • An experienced customer success engineer will have worked with MANY unhappy customers. If they are good at their job they should have at least one story of improving a customer’s view of a company.

• Experience w/ Command Line

  • This can give you a sense for how technical they are. This can also give insight if their background is Linux, Mac/Unix, and/or Windows. This is not a pass/fail, just an indicator of how much they might need to learn to get up-to-speed.

Programming Question

• Favorite Programming Language? Why? What is it Bad For?

  • It’s important to have this as a three part question. A candidate might be tempted to list a language your company uses or the job description stated. Every programmer has a favorite language, let them tell you theirs. If they didn’t state why, ask explicitly. This gives you insight into their knowledge of their “alleged” favorite language and their preferences. Finally, ask what the language is bad for. This last question is critical as it gives insight into how flexible an engineer is. If the candidate says Python (for example) is their favorite and it isn’t bad at anything they are clearly wrong. All languages have their trade-offs and weaknesses. A programmer who says their favorite language isn’t bad for anything could be unreceptive to using other languages when needed.

Senior Data Scientist

• ML experience?

  • I have almost no machine learning experience, so it was critical for me to determine what experience candidates had. I also had a data scientist ask more useful ML questions.

• Experience managing ML projects (including design)?

  • This was a critical part of the job role. I asked this to hear their history of leading their own projects.

• Programming experience w/ Data Science languages like Python, MATLAB, and R?

  • These match the languages that were on the job description. This gives a sense for how much they might need to learn for the job.

• Database experience?

  • Does the candidate have experience with the row-based and columnar databases your company uses? Do they have equivalent experience? Do you have time for them to learn your database stack on the job?

Senior Software Engineer

• Mentoring experience?

  • I generally expect senior engineers to spend time mentoring interns and non-senior engineers. Are they comfortable with that kind of work? Do they seem to have enjoyed or loathed it?

• Feeling about support work?

  • Most engineering roles have an amount of support responsibilities that could include being on-call and working directly with customers. Are they open to this kind of work or would they prefer doing greenfield work?

Management

• Example of how an employee’s career has evolved?

  • I want to see that a perspective member of the management team has experience and interest in growing employee careers. This can give you a sense if the candidate is autocratic or a servant leader.

• D&I initiatives that have failed and worked?

  • This will give you a sense for their interest and commitment to diversity, equity, inclusion, and belonging. This might also give you ideas for initiatives to copy or have them implement if they are hired!

• Retention Strategy?

  • This can give you another sense of their leadership style and how they value employees. Do they work to make employees happy? If an employee’s growth is limited in the company are they willing to help them explore outside the company? Have they written LinkedIn recommendations, showing the world how much they value their employees?

• What do you enjoy about leadership?

  • This can give you a sense in what motivates the candidate and again what their leadership style is.

I get a lot of job search questions, so here is what I’ve learned in active searches. This article originally appeared ten years ago on Google+. I migrated it to LinkedIn five years ago when Google+ was being retired. This update includes some AI tips.

In my first active search, very few of my co-workers at MEDITECH knew I was searching, my boss Daniel Deftos did. He supported me in finding out what was best for my career. I enjoyed my time at MEDITECH and saw after I left how well they had developed an inclusive culture, which at the time I took for granted.

I began the job search in late December 2013 and got an amazing offer from Carbonite in late April. At the time the average job search took 6 months. I learned a lot along the way and interviewed with some really cool companies.

If you want to get a job the two most important things are networking and your resume. These are the keys to getting you an interview. A good resource for networking is Blue Sky Resumes, check out their guide about LinkedIn:

http://blueskyresumes.com/blog/7-linkedin-mistakes/

LinkedIn (LI) is the best job networking site. You should be on the other sites too (Career Builder, Monster, Craigslist, Dice, etc). In December 2013, I had about 400 LI connections and upgraded my account to Jobseeker Premium. When I completed my search I had 1,375 connections. As of 2025 I have 6,546 connections. I've gone from following LinkedIn's advice of only connecting with people I've met in person to being an open networker and back to limiting who I connect with. The only people I'm likely to disconnect, or not connect, with are people who are clearly trying to scam or spam. I tend to go back and forth between paid and free accounts depending on if I’m looking for employees or new roles for myself.

Resumes

My friend Stever Robbins is, what I describe as, a life coach. He had a podcast called "Get-It-Done-Guy". You should listen to his 4 podcasts from December 2013 on resumes.

No matter how many times I heard and read that resumes should be individualized for each company and that they should have bullet points starting with action verbs followed by nouns, it was Stever that got me to understand. Here is an example of bullet points from the resume that got me the interview at Carbonite:

• Gave managers real-time high-level view of status of 400+ projects and 40 applications by implementing Jenkins, a continuous integration server to automate builds and escalate build problems to the appropriate engineer.

• Integrated Jenkins open-source CI software to MEDITECH internal technology.

• Developed performance metrics. Increased speed by parallelizing work. Decreased build time 93%.

• Collaborated with stakeholders throughout the company to communicate and insure progress towards needs of our internal customers, the software development staff.

• Verified goal achievement via demos to stakeholders.

• Facilitated backlog grooming meetings with stakeholders.

• Specified new workflows and internal development tools.

• Reviewed functionality and efficiency of existing development applications to identify and resolve functional and usability gaps between existing and new systems.

AI can make this a faster process for you. Give your AI agent a copy of a generic resume and the job description and ask it to make a tailored version for the company. It’s critical that you proof-read it though. If there is anything false or that you don’t want to discuss in an interview cut it. After the creation of the custom resume then ask the AI agent to also draft an intro email. I know this sounds very impersonal, but keep in mind that it’s using your data and the job description as a source. For the email you definitely want to make edits to make sure it is consistent with your “voice”.

Another powerful use of AI can be to ideate on career opportunities. If your industry is contracting you can ask it to review your skills and suggest jobs that would fit your interests and talents. You might want to give additional prompts to refine suggestions. As an example, say it suggests some international roles but you want to stay local, tell it that moving isn’t an option at the moment and what options might be closer to where you live.

Networking

Having friends at your target companies is a great way to get noticed. More people get hired this way than from sending their resumes to places they have no contacts. LinkedIn is a great tool to see who you know at a given company. I got interviews at GSN Games, Amazon.com, and Google all through friends. My strategy was to check job boards (mostly Dice, ZipRecruiter, and LinkedIn) and when I saw a job that interested me I would do some research. First, I would check to see my connections on LinkedIn. If I had any I would ask them about the company and for a referral. Most companies offer bonuses for employee referrals, so don't feel like you are asking for a huge favor when you ask for a referral. Second, I would read reviews of the company on GlassDoor. Any company that was less than 3 stars on GlassDoor I would pass on.

While I have lots of well connected friends, it was actually external recruiters (AKA: vendors or the less polite term "Head-Hunters") that got me the job at Carbonite. Some external recruiters are amazing. For example, Jill Zinner is a friend of mine from the game industry and she was able to show me how bad my original resume was and pointed me to Blue Sky Resumes. I enjoyed working with several other vendors including the staff at JobSpring and the staff at WorkBridge.

Carbonite

I had heard of Carbonite several years earlier via a web advertisement for their software. I remember, at the time, thinking that was an awesome name for a backup software company. I had found Mark Goodstein of Techpros on LinkedIn. He had called me and we had a long discussion about what I was looking for. He also gave me some more resume advice (which led to the version that got me the Carbonite interview). He also introduced me to his co-worker, Lauren Greenhow. When she first called me about Carbonite, I was luke-warm about the opportunity. At the time I was interviewing at Amazon.com for a manager role and at Google for a programming role. I agreed to interview with Carbonite and she setup an interview between me and Kanda Alagappan.

Kanda is the perfect person for his job! Interviewing for him was a joy. He made it clear what Carbonite's culture was like and why I wanted to join the team! Prior to that interview, both as a candidate and a hiring manager, I had never laughed so much in an interview before.

I like to point out that without vendors (AKA: head-hunters) I never would have gotten this job. I had not seen a post for it. The real irony of how I got connected with Carbonite is that I have one very close friend and one acquaintance that were working there when I interviewed! I hadn't realized this until after my screening interview with Kanda. The lesson, it doesn't matter how great your network is, vendors are an amazing resource.

Final Thoughts

If you have not already, connect with me on LinkedIn. While I’m no longer an open networker, the only way I would deny a connection request is if you were obviously trying to scam or spam people on LI. I have a ton of 1st degree contacts that are recruiters. Friending me will make you 2nd degree contacts to them. The LI search is based on relationship closeness. The closer you are to somebody the easier it will be for them to find you.

If you’re interested in a job let me know. I can obviously help you with Home Chef, but I have several vendors who I've made friends with that are looking for talented people.

This was originally posted on LinkedIn in December 2022 and has been updated.

In late 2022 we had a swath of layoffs because of investors realizing that many of their investments weren’t working towards an income positive model. I think organizations struggle with ethics for multiple reasons. Our VC pipeline and capitalism in general makes the expectations of shareholders unsustainable.

When money is tight (say because of Schrodinger’s tariffs), companies have two options to survive; reduce costs or increase revenue. Companies get into these situations when markets shift and costs increase. Leaders should strive to do their best to predict these shifts and steer towards financial stability. Forces impede these efforts like the want to win big, the Ikea effect (in this case meaning entrepreneurs thinking they have a valuable product when in reality there is no market for it), and shareholders wanting risks that lead to big rewards. Historically, shareholders preferred dividends to share value, then companies like Intel and Microsoft set a standard of reinvesting all profits into the business. This practice means there is almost never a financial safety net of cash on hand or the option to just give shareholders less (because most companies these days give nothing).

The sooner you see changes are needed the more options you have and the more thoroughly you can plan. Being transparent will be critical to how you're judged as a leader. Transparency also enables a wider pool of people who can offer advice.

The first layoff I survived was years before the pandemic. I was the DevOps Lead at a small startup. As soon as it happened I realized there were several ways I could reduce costs for the business. We had been outsourcing IT work that I could easily handle so we ended that contract. I also found we had several redundant services (multiple repository hosts and multiple monitoring services). I eliminated those redundancies. We had been historically keeping the same amount of AWS instances running regardless of their use. I implemented automation that turned off employee servers during off hours and introduced auto-scaling based on our server load. Finally, I saved us some money by using AWS reservations. All of these efforts combined saved the company more than my salary. Had I known prior to the layoff that we were spending too much I might have been able to save at least one job. While not all employees are in positions to save this amount of money, there are enough to warrant transparency. Sales people might also be able to propose pricing changes and ways to onboard more customers.

Often companies hide their financial status to protect share prices and limit employee attrition. This might feel like it helps in the short term but when the news eventually breaks employees and shareholders will feel duped. It will be a break of trust that may be impossible to repair. Some shareholders might panic and sell. The employees who stay will work at a diminished capacity due to stress and survivors' guilt. Many employees will go on job hunts. Employees will consider organizing and at some companies unions will be formed.

Repeatedly companies avoid transparency to get employees through a big release or a major sales event like Black Friday. After the milestone has come and gone they feel they don’t have time to explore options other than layoffs. This makes employees feel like leaders were trying to keep morale up while squeezing one last bit of productivity out of them.

Many companies try to foster a family feeling. As experts point out on Harvard Business Review podcasts, you can't layoff a family member. The instant a layoff happens the family illusion will disburse.

When announcing a layoff companies want to reassure employees to prevent voluntary attrition. They then say things like, "we have tons of money in the bank," and "this layoff means it won't happen again." If you have plenty of money in the bank, why did you have a layoff? If there was no transparency leading to the layoff there is no reason to trust there won't be another, and if there is another, people will walk.

MEDITECH upper management liked to use the phrase, "don't fire us and we won't fire you." They were founded in 1969, and to my knowledge have never had layoffs. While attrition was low, the hope behind the phrase was that employees would talk to management before considering leaving. Similarly, we gave under performing employees a lot of notice they were at risk and provided them guidance for improving.

In 2020, many companies laid off a disproportionately large number of LGBT employees just prior to Pride month and then for Pride month temporarily changed their logos to have rainbow themes. Allies and queer candidates now avoid companies like this. Netflix faced public criticism that could impact subscriptions for targeting a layoff to queer and non-white departments.

If cutting costs are required to keep the business running you should give people very transparent options including furloughs, pay cuts, and voluntary attrition. As a manager, I've been happy to choose myself for a layoff over my employees. Morale and loyalty is going to be higher when employees can be part of the decision making.

Lastly, it's critical that executives "feel the pain." When the Wii U didn't meet sales expectations Nintendo's CEO voluntarily cut his salary in half sending a message that he was in it with all the employees. As leaders, we are ultimately accountable for the performance of the business. If we miss sales targets it is in part the fault of the head of sales, if we create less leads than planned it's partly due to the head of marketing. For engineering, if we don't meet our service level objectives, if we have more bugs than promised, if we fall short on our delivery commitments it's partly the fault of the head of Engineering. The CEO and board of directors all take ultimate responsibility for these issues. They also are ultimately responsible for overhiring. Nobody will want to follow them if they don't own up to their part in the mistakes. We're all human, it's okay.

This was originally posted on LinkedIn in January 2023 and has been updated.

As a leader, I believe the very first conversation with a candidate, employee, or mentee should include the question, "where do you see yourself in 5 to 10 years?" For a candidate, you need to consider if the role you are working to fill can be a stepping stone for them. If it can't, it's probably best to let them know and suggest alternative positions, or companies, they could interview for.

In my 1:1 template I have a recurring topics section that includes long term goals. I make sure we talk about them at least once per quarter. The goals are often updated, sometimes to have more specificity, sometimes to reflect changes in interest, sometimes to add new goals, and sometimes to remove goals that are complete or no longer relevant.

I always end a formal performance conversation with a review of long-term goals so that I can make sure I understand what an employee might work on to help with those goals prior to the next evaluation.

Not every assignment is going to help with long-term goals. When an engineer wants to become a staff software engineer, cross-team project work can be critical in making a promotion case. If the plan for the next few months is bug reduction, or projects only impacting the team, it can be more challenging to find that employee work that pushes the needle for them. It’s critical to be transparent about how the road-map might not be helpful to their career goals and recommend options like mentoring outside the team, giving lunch and learns, and getting involved in cross-team initiatives unrelated to the road-map.

Even when a road-map is aligned with an employee’s goals there might be multiple employees who need the same type of work and there will still be emergent work that needs to get handled. It’s critical that work assignments are equitable.

It may feel counter-intuitive but it’s critical for your employees to see that you truly want the best for them even if that means they leave your team or company. That loss may hurt in the moment but it’s far better than what will happen if an employee and team stagnate. Employee’s who are held back will become resentful, may “quiet quit”, give bad reviews of the company, and leave at the earliest opportunity.

My biggest success as a leader was with an employee I had at Affectiva. She had interned at Google the summer before she interned with our science team. She graduated at the top of her class at the American University of Cairo. I heard she was graduating just as I was building a data team. The science team wanted to hire her but had no openings so I reached out to see if she’d be interested in doing data science work. As is often true with candidates I’m excited to hire, I was nervous to interview her. After I hired her she dug into the work spending several months making systems to enable active learning and rapid labeling of video data. Eventually the data team got so large that we spun it off into its own group while I refocused on the engineering teams. A year and a half after I hired her she had an opportunity to go to Stanford as a Knight Hennessey Scholar. I happily agreed to write a letter of recommendation. While I was sad to see her move on, it's been awesome to see her continued success.

Stephen Covey makes several good points in The Seven Habits of Highly Effective People, including how to prioritize time using the four quadrants of Important + Urgent, Important + Non-Urgent, Not Important + Urgent, and Not Important + Non-Urgent. Above is an example I developed for this article. While urgent tasks have to get done, non-urgent tasks are important and beneficial too. For example, changing a diaper is urgent, it has to be dealt with right away. At times, we can feel overwhelmed by urgent work. Non-urgent work can prevent some urgent work. For example, the non-urgent task of changing oil will make sure I don’t have to deal with an urgent issue like my car engine overheating. The non-urgent task of relationship building with children can help reduce the number of urgent tasks to repair relationships that weren’t fostered. The time spent on non-urgent tasks often leads to new opportunities.

Sometimes a non-urgent activity can seem unimportant but in a given context be important. As an example, playing video games is often not important. When my kids were young they needed help with hard sections of video games and helping them improved our relationship. Similarly playing online games with them now that they are older maintains our relationship.

Companies over a certain size (let’s say 500 people) usually have a leveling rubric defining the expectations of each title. It’s critical for individual contributors and managers to push for the document to stay relevant as the company changes. When I make a promotion case, it is because I can prove that an employee meets 25% - 75% of the expectations of that next role. I’m transparent with employees about where in the rubric they have growth opportunities to meet their next career goal.

As a leader, I discuss the four quadrants, with all employees when we discuss career growth. All of the promotion announcements I have ever written discuss the important and non-urgent work the employee did, like mentoring, architecture work, and managing major successful projects.

While this article talks a lot about getting promoted, I want to make it clear that there are alternative strategies to success. A person needs to deeply consider the pros and cons of climbing a corporate ladder. The higher one is the more autonomy they tend to have. Generally pay is better at higher levels. On the flipside, there is more ambiguity, more stress, and sometimes more time expectations. Every person has to decide for themself if those pros outweigh the cons. Continuing to be a strong performer without moving up the ladder is valued by many companies and employers. Ideally employees have a choice to change their mind if the promotion isn’t what they continue to want. Having satisfaction at the bottom of the ladder is especially important for careers that have few leadership opportunities, like education. As a leader, it’s important to show what value a person might have by staying where they are.

In summary, leaders need to make time to regularly discuss the goals of employees to find ways to connect those goals with the goals of the team, the product or service, and the company. To help an employee succeed you can use tools like the four quadrants and a rubric to outline their path to the next milestone. Employees should be mindful of the rubric (especially for their role and the role that succeeds it). If you don’t have a rubric try creating one with your peers so you can define standards and expectations for the positions in your department.

This was originally posted on LinkedIn in September 2021. The original has some less inclusive wording that I’ve improved upon here.

When I'm asked to describe my leadership style I talk about how I strive to be a servant leader. I once attended a training for a regional Burning Man event where one of the instructors described servant leadership using an inverted pyramid. The leader is on the bottom of the pyramid and the members of the team are on the top. Coaching, mentoring, and removing obstacles are how the leader can provide support to the team.

Unblocking

It’s important to preemptively remove blocks before they impact the team. For a new employee there are several things that should be done before the first day:

• Hardware (ie: a laptop) is configured and delivered to the employee

• Accounts (ie: Slack, Google, JIRA, etc.) are created

• A 30/60/90 day plan has been developed as a guide

• Scheduling:

  • The employee has been added to all group meetings

  • An introductory meeting with the manager has been created and one with the skip level manager

  • A recurring 1:1 meeting with the manager (ideally weekly)

  • The employee has been scheduled for required trainings

  • A mentor has been assigned (sometimes myself and sometimes another member of the team)

  • Onboarding documentation is up-to-date with any changes since the last new hire joined

Another way to prevent obstacles is to shield the team from distractions. Sometimes this means fielding questions and paperwork for the team. Sometimes this means taking the heat when a customer is upset. Sometimes this means pacing when outsiders interact with the team.

Agile frameworks, like scrum, have natural ways to highlight obstacles. Tracking software often has settings to mark tasks as blocked. Scrum has multiple ceremonies where obstacles can be discussed:

Refinement

Requirements are often brought to light during a refinement session. Ideally these dependencies are linked to the work within the tracking software. For internal dependencies, the backlog of work may need to be re-ordered. If there are dependencies discovered that are the responsibility of other teams those dependencies have to be resolved before the work can be completed (and in many cases even started). Depending on the team’s structure these dependencies can be the responsibility of the product manager, the team lead, or the engineering manager to work out with the other team. Customers may need to be notified about how these dependencies will impact the release schedule.

Sprint Planning

When a sprint (which is what we call blocks of time in Agile) is being planned each story being pulled in needs to be checked to see if there are any outstanding requirements that need to be resolved. If there are unresolved requirements the team needs to decide if it’s possible for both the requirements and the story to be done within the sprint.

Syncs

The person running this meeting (often a scrum master) is responsible for asking each person if they are blocked during daily 15-minute sync meetings. Often whatever is blocking a person can be resolved by the team during sync. For some obstacles the product manager may need to work with stakeholders to further refine specifications. Other teams may need to be contacted to help remove the obstacle (for example if a developer is blocked because their laptop cannot boot IT might need to be contacted).

Retrospectives

A retrospective is a great opportunity to discuss recurring obstacles (like the network goes down every Friday at 3PM JST or the product manager keeps changing the acceptance criteria after work has started). Psychological safety is critical to the success of these meetings.

Mentoring

When I’m serving as the dedicated mentor to a member of the group I aim to have up to 40% of my time available to the mentee. Some people consider mentoring a distraction to their work. When a member joins a team, or project, they cannot be impactful until they are up-to-speed. The time it takes to get them up-to-speed may slow the mentor down (up to 40%) for a few months but ultimately that investment will improve the team velocity as the mentee takes on work.

Approach-ability is critical for a mentor. If a mentee is told by a mentor, “I can’t help right now,” multiple times in a row, the mentee is liable to give up and flounder. When a mentee approaches me, and I have to turn them away, I make it a point to tell them when I expect to be available and reach out to the mentee when that time comes.

If a mentor needs to be “heads down” at times then it is their responsibility to tell the mentee when they are available. This can be done formally with scheduled mentor “office hours”. This can also be done less formally by stating times of the day or week that are off-limits for “focus time”.

Mentoring requires psychological safety to ensure honest conversations about a mentee’s challenges occur. Often when a mentee comes to me with an issue I’ve also struggled with I’ll tell them how I also found it challenging. It’s important for mentors to flag their own fallibility.

Mentoring has to be about “teaching to fish”. Sometimes I need to slow down so I can review the steps that lead me to a decision. The mentee needs to know how to take those steps solo and make their own conclusion. While it can be tempting to just “do the work” or point to a solution, the extra effort of showing how to find a solution will pay huge dividends for the team.

Coaching

Most of my coaching is done in 1:1 meetings. In an initial hiring manager interview, or first meeting with an employee, I ask the employee about their 5 - 10 year goals. We revisit those goals regularly to discuss how upcoming work can help, or hinder, meeting those goals.

I urge all of my employees to have a comprehensive LinkedIn profile. For interns I also often help them refine their resume. Depending on career goals, I sometimes help interns to decide what jobs to apply for and how to orient their resume to the job description.

I assign employees an amount of work that is geared to their personal goals. I also include formal goals in written reviews that align their personal goals with the team, the product, and the company. I outline how this work can further their career. When an employee gets to the point where they are ready for the next step in their career, if that step cannot be within the group, I help them to find internal and external opportunities.

Summary

I’m surprised how many styles of leadership there are. I’ve heard of managers who have reported their style to be dictatorial. It’s my hope that after reading this article you have some new ideas of how to coach, mentor, and unblock your team.

For more advice and ideas message me on LinkedIn.

Moriko discussed how to avoid group think, reduce conformity bias and reduce authority bias. She also gites tips for retrospectives and 1:1s.

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

• HBR IdeaCast - https://hbr.org/2018/01/podcast-ideacast

• Coaching Real Leaders w/ Muriel Wilkins - https://hbr.org/2020/12/podcast-coaching-real-leaders

• > Code - https://www.greaterthancode.com/

• Dear HBR - https://hbr.org/2018/01/podcast-dear-hbr

• Code Sw!tch - https://www.npr.org/podcasts/510312/codeswitch

• WorkLife w/ Adam Grant - https://www.ted.com/podcasts/worklife

• Maxwell Leadership Podcast - https://johnmaxwellleadershippodcast.com/

• Leading with Empathy & Allyship - https://empovia.co/podcast/

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

• Rich Dad Poor Dad by Robert T. Kiyosaki and Sharon Lechter

• Uncompromising by Steve White

• His website, Corporate Dad: https://www.corpdad.com/

• His Upcoming book: LinkedIn Professional Brand Guide and Planner

• That we interview McKenzie Robuck Walsh ( https://www.linkedin.com/in/mackenzieroebuckwalsh/ )

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

• The Coaching Habit's website: https://boxofcrayons.com/the-coaching-habit-book/  

• Box of Crayons - The learning and development company that Micheal works at: https://boxofcrayons.com/ 

• Barry Schwartz's TED Talk based on his book, The Paradox of Choice: https://www.ted.com/talks/barry_schwartz_the_paradox_of_choice

• i done this - the app I mention in the episode: https://www.idonethis.com/

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

• Grindr is hiring and will be launching it's internship program shortly: https://www.grindr.com/careers/  

You can learn more about Dana at her LinkedIn: https://www.linkedin.com/in/dana-rose-ross/

Dana suggests we interview Megha Bambra ( https://www.linkedin.com/in/meghadhall/ ) and Joel Keating ( https://www.linkedin.com/in/joel-keating-286a043/ ).

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

Ray Recommends:

• Connecting with Ray on LinkedIn: https://www.linkedin.com/in/raymondcmartinez/ 

• Speaker, coach, and author Simon Sinek: https://simonsinek.com/ 

• Gifford Thomas’s leadership first writings: https://www.leadershipfirst.net/ 

Ray suggests we interview speaker and workshop facilitator Sean Ilenrey ( https://www.corpdad.com/ ).

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

Lance Recommend reading Radical Candor by Kim Scott, a book about giving feedback. For Lance’s newsletter on managing personal finances please visit lancewilkinson.com . Lance suggested we interview Izzy Piyale-Sheard.

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF

• Forest Handford

  • Is the author of A Trans Feminist's Past and she wrote some novels including Flipping.

  • Forest has over a decade of corporate and volunteer leadership in which she's learned a lot and hopes to share those lessons with listeners.

  • She's currently looking for a new leadership role. If you have one in mind, please message her on LinkedIn or Discord. Once she starts a new role the timing of episode releases may change.

• What is Practical Leadership Cast?

  • For at least the first few episodes the format will use an interview style with Forest as your hostess. After that we might change up the format and potentially have multiple hosts.

  • Practical Leadership Cast is about practical leadership topics like mentoring, coaching, recruiting, and DEIB.

  • The initial episodes will interview friends and former colleagues.

  • We have a Discord server, please join to be part of the conversation.

  • Want to get involved? Let us know on our Discord!

  • For the moment we are not monetizing. This may change, possibly with a Patreon.

Music credits:

• The opening music is Like a Prism by Miyagisama .

• The closing song is Something About You by Marilyn Ford .

Thanks for listening. Please rate, subscribe, and share. Join the conversation in the Practical Leadership Cast Discord server: https://discord.gg/ewhPY6akRF