Category Archives: leadership

career, leadership

the work you love and the work you don’t

In the current tech jobs market, I’ve talked to a lot of folks who were looking for their next role. Instead of simply diving straight in and looking for something very similar to their previous role, I think it’s worthwhile to take a step back and be thoughtful about what that next role should be. Besides analyzing your day to determine what gives you energy, an exercise from the book Never Search Alone sets out a thoughtful framework for considering what’s next.

In this exercise, you write out the things you love doing at work, and the things you hate doing at work. I think that it’s important to write this out and then let it percolate for a few days. I’ve found that additional items on both lists arise later on, or that I come up with a different way to express something. If you also did the exercise from my previous post about what gives you energy, you might have already identified some of the things you love and some of the things you hate.

For example, here are some items from my list of things that I love doing:

  • Having a deep understanding of our users and our market to create innovative products and services
  • Meeting and exceeding the expectation that a design executive will influence and contribute to product strategy, engineering strategy, and business strategy.
  • Coaching, mentoring, and upskilling my organization in their technical and professional skills. Creating cross-functional mentoring and coaching opportunities.
  • Having processes that work in our environment to make our jobs easier without adding onerous overhead

And here are some items from my list of things that I hate:

  • Working in a feature factory where the only measure is on the number of features we spit out. 
  • Working with people who are jerks: antagonistic, not respectful, not accepting of other backgrounds or experiences, creating unnecessary conflict, unable to give or receive constructive feedback.
  • Decision-making by committee.
  • Working on something that doesn’t make people’s lives better.

The book then has you analyze these two lists and coming up with two more lists: what your next role must have, and (just as importantly!) what your next role must not have.

Here are some of my must-haves:

  • I must work for a company that appropriately invests in its future through product discovery, a deep understanding of its users, and engineering excellence.
  • I must work for a company that understands the value of design as more than just “making things pretty” and expects design to have a role in crafting business strategy.
  • I must have a manager who respects me and the disciplines that I represent, understands how we contribute to the business, and creates opportunities for growth.

And some of my must-nots:

  • I will not work for an asshole again.
  • I must not work for a company that does not value the craft of management.
  • I must not work in a field or on technology that I think makes the world worse.

If you’re searching for a role, these lists are a framework to help you evaluate the opportunities that come your way. You’re probably not going to find a role that meetings all of your must-haves and your must-nots. You can use this to help you decide whether it meets enough of each of them to be worthy to consider. It also can help you negotiate for more things on your must-have list and reduce the things on your must-not list. This is an especially good input into the evaluation of job descriptions that I describe in this post.

I’ve found that I have to pay close attention to my must-not list. I am prone to only looking for the items on my must list, but ignoring the items on my must-not list. Having a complete picture of how well any given role fits what I want and what I don’t then gives me the ability to decide what trade-offs I want to make. It also gives me negotiating points: I can say that I’m really excited by this role, and I would like to work on a way to incorporate something from my must-have list that it’s currently missing so that it’s an even better fit for me.

By doing this reflection, I’m better prepared for interviews about a new role. I can evaluate job descriptions against my lists of must-haves and must-not-haves. Then I can also identify open questions about whether it has additional items on those lists. That gives me prompts for what I should be looking for during the interview process.

leadership, management

managing through layoffs

Layoff. Reduction in force. Redundancy. No matter what word you put on it, a layoff is one of the hardest things for a manager to lead through. It’s natural to feel overwhelmed in this situation, regardless of whether you’re the decision-maker on who is leaving the company. You will have your own feelings about what is happening, at the same time that you’re working to support team members who are leaving and team members who are staying.

When you’re a manager in this terrible situation, give yourself grace. Take time for yourself. Invest heavily in self-care for the next few weeks. (Yes, weeks. The impacts of a layoff are long-lasting. I’m sorry.) If you’ve got a therapist, spend time with them. If you don’t have a therapist, this might be a good time for that. Whatever you do, do not dump your feelings down on your team. Don’t hide that you’ve got feelings, rather don’t dump on them. Your team needs to see you handling this situation empathetically for those who were laid off and those who remain.

While you’re giving grace, make sure to give some to your peer managers. They’re also dealing with lots of difficult things. Check in 1:1. Managers often don’t get a ton of support in a time like this, especially if their team was relatively lightly-impacted, but they’re still dealing with the survivor syndrome of themselves and their team, plus trying to figure out how to move forward. Give your peer managers some space to say the things that they can’t say to their directs, and be vulnerable with trusted peer managers too.

Whenever you talk to your Human Resources business partner (HRBP), give them some extra grace. Layoffs are terrible for HRBPs. They’re dealing with the worst of this situation. If you’ve got a good relationship with your HRBP, offer them some safe space to talk/vent/whatever.

In the weeks after the layoff, you will probably see some problematic behaviors amongst your team and others. Some folks are going to throw themselves into their work to have somewhere to channel their feelings. Some folks are going to throw themselves into their work because they’re terrified of getting laid off next. Some folks are going to disengage for a bit. Be prepared for all of that and do what you can to redirect the unhealthy behavior. If your employer has any benefits like an employee assistance plan (EAP), this is a great time to refer folks to it.

Folks are probably going to be on edge for a few weeks, or even longer. You will probably see an increased amount of interpersonal tension and stress behaviors. Be ready to manage that. Any big internal event or milestone, like a launch or review time, will probably cause more of those emotions and behaviors to bubble up. By being prepared for this, you can help divert behaviors away from unproductive or toxic ones. Many of the folks who remain might be nervous about the future of the company and whether there will be future layoffs. When you’re asked about these, be honest about what you know and what you can share with them.

You might find that your team has reduced trust in you because they believe (rightfully or not) that you must have known something in advance or must have made decisions about who to keep. They might think that you should have done more to prevent the layoff. You will have work to do to regain their trust.

This is one of the awful times of management. You can get through this.

leadership

the fine art of delegation

As a leader, delegation is one of the most important things to do. You have to learn how to delegate effectively, what to delegate, how to support someone who you’ve delegated to, and how to hold them accountable. As a recovering perfectionist, I’ve also had to learn how to let go of how I imagine I would do a task if I had infinite time and resources so that I don’t measure success against that.

When I’m trying to decide whether to delegate a task, and what to do if I think the person who I’ve delegated to is having some trouble with it, I ask myself the following questions:

  1. Does this task need my effort where I would (of course) do it flawlessly, or does it need someone’s effort where if they do it to even half as good as I would have done it, it would be good enough?
  2. Does this task need to have more people trained up in how to do it?
  3. Could this task benefit from having someone else do it, who might bring a new perspective or an improvement to it?
  4. Does the person who I’m delegating to need to grow skills in this area, and this task will help them grow, even if there are growing pains?
  5. Does someone else or a team need to learn that I’m not the only competent person available to them, so they have to be comfortable with the work output from other people too?
  6. Do I actually have the time to do it?
  7. Is this actually the thing that is best for me to be spending my time on? ie, what’s the opportunity cost of me doing this task?

This list helps me be mindful of spending my time in the right place, creating opportunities for others on my team to grow their skills, and right-sizing effort and expertise to a task.

leadership, management

evaluating the performance of managers

One of my mentees, a newly-minted director, asked how to evaluate the performance of the managers who now report to them. We were discussing some of the differences as you move from manager to director and how to make the shift in mindset.

Measuring the effectiveness of individual contributors (ICs) is relatively straightforward. Are they getting their work done? Are they helping others get their work done? Are they helping those around them build their skills and be more effective? Are they taking feedback? Are they giving high-quality actionable feedback? Measuring the effectiveness of managers, though, feels a bit harder.

Manager performance questions

These are the questions that I use to help me understand how well a manager who reports to me is performing.

How well are their ICs performing? If their team is performing well, the manager is probably doing pretty well. If their team isn’t performing well, what are they doing to turn it around? Are their ICs performing well only because, or possibly in spite of, the manager micromanaging them?

How is morale on their team? If their team is happy, the manager is probably doing pretty well. If morale is low, what is the manager doing to turn it around? Is the manager keeping morale artificially high, such as by not giving difficult but necessary feedback?

Do their ICs have the right amount of stretch assignments? Is the manager creating the right opportunities for their team to grow their skills?

How well is hiring (if any) going? Are they able to find a great slate of diverse and high-quality candidates for their roles? Are they following best practices in their hiring process?

How well is the manager working with and communicating to peer managers? This is such an important part of their job. What is the feedback that you’re getting from their peer managers?

How well is the manager communicating to their manager? Do you as their manager know what’s going on, at the right level of detail? Are you caught unaware by problems on or with their team?

Is the manager contributing to cross-team initiatives? Besides just getting the work done, you should have cross-team initiatives to help improve your organization and your company. Your manager should be contributing to these?

How well is the manager handling conflicts (within their team, between teams, between themselves and others)? Some days, it can feel like the job of a manager is only to be a mediator between conflicting parties. A good manager is managing those problems, coaching people through them to handle them better themselves, and reducing the risk that a conflict will spiral out of control.

How well is the manager assigning and delegating work? Are they giving the right work to the right members of their team? Are they doing so fairly and equitably? Are they delegating the right work from their list to folks on their team?

How well is the manager dealing with emergencies? There’s always some kind of emergency going on. Sometimes it’s work related, sometimes it’s personal, sometimes one creates the other. When an emergency of some sort comes up, is the manager handling it?

A manager is a force multiplier

What I find most important to think about in manager performance is that they’re a force multiplier. If that force multiplier is being used well, they’re likely doing their job well. If they’re failing in some aspect of their job, they could be a negative force multiplier. For example, a manager whose team is low-performing and they either can’t see it or can’t turn it around is a manager who is a negative force multiplier. It’s your job as a manager-of-managers to understand where your manager is being a positive force multiplier or a negative force multiplier, and coach them as needed.

career, leadership

the goal-setting conundrum

Setting career goals is hard, especially when it’s time to do it as part of the usual performance review cycle. As I’ve coached my teams through goal-setting, I’ve observed several different reasons why it can be hard to set goals. These reasons include:

  • Analysis paralysis. “I could work on any number of things, but which ones are the ‘right’ ones to work on?”
  • Future hazy, try again later. “I really don’t know what I want my future to hold, so I’m not sure what goals I should have when I don’t have a three- or five-year plan.”
  • Too much happening right now. “I’m already in a period of personal or professional upheaval and I feel like I am only barely holding on. I can’t think about the future because the present is already too much.”
  • Impostor syndrome. “I don’t think I’m actually any good at what I do today. I can’t set goals to help me address my perceived deficiencies because that would be revealing to someone else that I’m an impostor.”
  • Dreaming about leaving. “I think I want to do something different with my career that isn’t available to me here. I do have goals, but I don’t want to talk about them with you for fear of repercussions.”
  • In the zone. “I’m happy with where I am right now. I do not want to get promoted. I just want to come in, successfully do my job, and get paid fairly for that.”
  • No role model. “I have no idea how to do this because I’ve never seen anyone do it well. I’ve not really tried to do it myself.”
  • No point. “This is just HR bullshit. No one pays attention to my goals. I’m going to write them down today and then no one will look at them again until my next performance review.”

Once you understand the root of what makes writing goals feel difficult, you can use that to help craft the type of goals to set. Here are some strategies to unlock the goal-setting conundrum for the reasons I outlined above:

  • Analysis paralysis: You could make finding the “right” focus your goal. To do this, choose one of your potential goals and work on it for a set period of time, up to a month. If you really can’t choose one yourself, ask a friend or colleague to help, or even pick one randomly. At the end of the month, evaluate your progress, how you’re feeling about it, and what impact it has made. If it’s particularly impactful and you’re feeling great about it, you’ve got your goal. If not, you can choose another goal to try for a time boxed period.
  • Future hazy, try again later: You could make figuring out what you want to do your goal. Outline a handful of options for what your future might hold. Don’t be afraid to dream big! From there, you could have informational interviews with people who have followed that path to leverage what they learned along the way. Or you could create a payout matrix to help you think through which path you might want to take. You could create a set of experiments to help you decide what you want your future to hold.
  • Too much happening right now: Depending on why you have too much going on, you could set a goal to reduce the number of things on your plate. What can you offload so that you’re not so overburdened? If you simply can’t offload things, you could instead set a goal to reflect on your situation and what you’ve learned from it. These types of retrospectives can help you and those around you avoid getting into situations like this, better handle those inevitable times when it feels like everything is going wrong at once, or even simply recognize that this happens and sometimes all you can do is keep on keeping on.
  • Impostor syndrome: Setting goals to help overcome impostor syndrome requires vulnerability and support. You have to be vulnerable in admitting that you feel this way, and you have to have support from a good leader who will help you move past it. If you aren’t sure if you’ve got a good leader or you’re not ready to be vulnerable, one way to sidestep this is to leverage your career ladder. Look at the competencies for the next level. They’re probably the same competencies as your current level, but they have broader scope and impact. You can frame your goals in terms of growing to that next level. You could also set a goal about getting in-depth 360-degree feedback from those around you to help you better understand what you’re great at and what you’re not, if that’s not already part of your performance review. That might help you combat your impostor syndrome, or at least help you decide where to focus your energy.
  • Dreaming about leaving: This is another one that requires vulnerability and support. If you’re ready to be open that you’re thinking about doing something else, you can set goals to make that decision. If you’re certain that you want to move on, you can set goals that help you and your organization be ready to move on, such as ensuring that you’ve wrapped up a key project and fully documented all of that great knowledge that only lives in your head. If you’re still exploring options, you can follow the strategies above for “future hazy, try again later”.
  • In the zone: You could make your goals about cementing your place as a solid contributor. Potential goals include improving documentation, improving processes, or mentoring.
  • No role model: Ask others to share their goals with you. Personally, I like sharing my goals with my team so that they can see what I’m working on.
  • No point: You can choose to treat this exercise as only an HR exercise, or you can choose to treat this exercise as something that you do for yourself. Setting goals is about your professional growth. You have to reframe the exercise for yourself and not let poor implementations of goal-setting get in your way.

As you’re framing your goals, you can use strategies such as SMART goals to help you create meaningful goals that you can make progress on. After you’ve done that hard work, the next step is to create an accountability structure to help you make progress. I like to set up monthly check-ins on my professional goals with someone such as a manager, a coach, or a colleague. That external accountability helps remind me to invest time in my goals, and reflect on what I’ve learned as I’ve worked on them.

career, leadership, management

climbing the leadership ladder: from manager to director to VP

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Recently, I’ve been asked several times what I’ve found to be the difference of being a manager, a director, and a VP. Each of those roles is an interesting one with its own challenges. My thinking on this is heavily influenced by this blog post from Peter Merholz. In his post, he introduces what I think of as the three distinct modes of management: managing down, managing to the sides, and managing up.

Managing down is managing those who report to you, or through you if you’re managing managers or directors. Managing to the sides is working with your peers to communicate information, resolve issues, and make decisions. Managing up is the skill of giving your manager, whether they’re a C-level or a senior manager, the tools and information that they need to help you, your team, and your company be successful.

As a first-line manager, where you’re only managing individual contributors (ICs), almost all of your time is about enabling them to be happy and productive. About 60% of your time is directly managing them: keeping them on track, giving feedback, coaching them, making sure they’re working well together, etc. Another 30% of your time is managing to the sides: ensuring that you’re aligned with your peer managers, resolving conflicts, communicating status information, and removing roadblocks. The remaining 10% of your time is managing up: working with your boss to manage priorities, identifying additional resource needs, communicating status, managing the budget, asking them to remove roadblocks, and setting the strategy within your area of focus.

As a second-line manager (for simplicity, I’m going to call this “director”), where you’re only managing managers, your focus shifts. You’re no longer the one directly responsible for enabling a team of productive and happy ICs. That’s the job of the first-line managers who report to you. Now your role is to ensure that the teams who report to you are happy, productive, and working on the right things. For a director, I’d estimate that 40% of your time is managing down to the team: ensuring that your managers are being effective in their roles, coaching your managers in how to be effective coaches and leaders, communicating needed information, resolving issues, setting direction for your team, setting your team’s culture, and removing roadblocks within and for your teams. As a director, managing to your peers is more important than it was as a manager. I estimate that managing to the sides is about 40% of your job. This is ensuring that you and your cross-functional peers are aligned on strategy and prioritization, that you’ve got the right folks working on the right problems across your teams, and that you are removing roadblocks for your teams and for your peers’ teams. The last 20% of your time is managing up: working with leadership to set strategy, communicating needed information, advocating for your teams, identifying roadblocks that need leadership intervention, and so on.

As a third-line manager (for simplicity, I’m going to call this “VP”), where you’re only managing directors, your focus shifts again. Now your directors are the ones responsible for having their teams be happy, productive, and working on the right things. You are accountable for all of that, plus be part of the team responsible for setting corporate strategy, and delivering on the commitments that you are making on behalf of your team. This means that much less of your time is managing down, maybe 20% of it. Managing down involves is communicating strategy, coaching your directors, resolving conflicts within your organization and between your organization and others, setting your organizational culture as part of your overall company’s culture, and ensuring that your directors are aligned amongst themselves. Managing to the sides is still about 50% of your job. Now that it’s at another level higher, it is even more cross-functional. Now you’re setting strategy across the entire company, identifying opportunities for your company, setting policies, removing roadblocks across your org and for your partner orgs, and communicating needed information across the company. The last 30% of your time is managing up: working with the senior executive team on setting strategy, communicating, making decisions, representing the company, and so on.

Looking back at Peter’s original post, the percentages that he lists don’t match my experience. I think he’s underestimated the amount of time needed at each level to manage up and to the sides, especially at the lower levels. While Peter frames his thoughts in terms of design orgs, I’ve found in my conversations with other leaders as well as my own experience in managing engineers and product folks that it’s held generally true cross-functionally.

If the things that you love are communicating, unblocking, and coaching, you must do more of that at higher levels. The shift that you’re making at each level is that you’re more abstracted away from your core discipline, and that you’re seeing and making decisions on a much broader swath of the company and the business. You are responsible for making a lot more decisions, often with less information than you  would like. I’ve found it to be a lot of fun, and a lot of responsibility.

leadership

leadership lessons from Mike Kruzeniski

Tomorrow is the one-year anniversary of the death of Mike Kruzeniski. He’s been on my mind a lot in the past couple of months, not only because of this anniversary.

I got to know Mike when he became my boss. He was hired as the very first VP of Design and Research at Included Health. I was a bit nervous during my first few meetings with him, balancing making him feel welcome in his mid-pandemic start, showing the value of my research team, and helping him get acclimated to the new company. He quickly won me and the rest of our design and research teams over.

Mike cared deeply about the craft of design. He wanted design to be beautiful and powerful. He bonded quickly with the designers and encouraged them to uplevel their skills. He gave them space to be creative and to push the boundaries. He didn’t hesitate to roll up his sleeves and get into the details. The design team flourished under him.

I have to admit that Mike’s care for the craft of design gave me pause when he started. I’ve worked for multiple design leaders who pushed designers to greater heights of creativity, and in doing so relegated user research to doing nothing more than validation research to prove how creative the design team was. Not Mike: his support for user research was boundless. He knew when and how to use research. He understood the value of generative research. He knew how to talk about its value to the executive team. He never talked about the design team, but rather the design and research team. My research team loved him just as much as the design team did.

One of Mike’s top strengths as a leader was that he believed in his team. He didn’t second-guess. He asked coaching questions if he thought that something hadn’t been considered. He always made it clear that not only did he trust his team, but he was also all-in on their success. I was the beneficiary of the opportunities that he created for me to grow my skills. At first, I didn’t even realize that it’s what was happening, but quickly came to see the pattern in as I observed him do it for me and for many others across the design and research team.

In addition to his innate belief in his team, Mike was vocal in sharing that belief. If I ever admitted that I was anything less than completely confident that I was going to be successful in something, he was there to cheer and to support. One of Mike’s friends called him the antidote to impostor syndrome, a description that I must agree with. He gave ongoing feedback and advice while reminding me that he believed in me and had no doubts that I could do it.

Although I didn’t get nearly as much time with Mike as I was hoping to, I still learned so much from him. His leadership style has informed a lot of who I am as a leader today. When I was first offered the promotion to VP of Experience Design at Babylon Health a couple of months ago, I immediately wished that I could call him and get his thoughts on making that transition.

I wish I could call him and thank him for everything. I’ll have to try to do him proud instead.