Management for first-time managers

The most important skill YCombinator doesn't teach founders

So much of the time companies spend during the YCombinator batch focuses on how to better serve your customers and how to fundraise, and the important topic of how to manage people is largely excluded. At the earliest stage, this makes sense - most companies fail because they never get to product market fit or fail to raise money to give themselves a shot. But right past that step, leading, motivating, inspiring, and managing people becomes the next big lever for your startup’s success. If you can do this exceptionally well, you can scale yourself and your team to become orders of magnitude more productive than doing this average or poorly. But what’s the difference between mediocrity and excellence in management? And how do you actually do that?

I started my career as a management consultant at Bain & Company. One of the unique specialties of management consulting is they consistently optimize management to a science. The entire model is predicated on churning through super smart new-grads right out of college, training them quickly, and then sending them off in 2-3 years when they are ready to move on. If you know you will only have two years with someone, you want to optimize how to make them as productive as possible as quickly as possible. Bain did this really well.

By comparison, management across the tech industry tends to be pretty poor (though there are certainly exceptions). In my five years at Meta, working in teams from Facebook growth, to ads, to Oculus, to Instagram, I rarely saw management that compared to my experience at Bain. As I’ve coached founders with backgrounds across tech from the major companies to startups, I realize few people have examples of what great management looks like. I attribute this to the fact that in hyper-growth companies, the best individual contributors are promoted to managers and often not given mentorship as to how to do that well, possibly because the person above them has only been a manager for a short period of time and never learned to do that well. Throw in the cultural beliefs in meritocracy and radical independence (”I can figure anything out myself”), and you’ve got a potent combination for mediocre management.*

The rest of this piece will cover my perspective on how to become an excellent manager in an early-stage startup. This perspective is targeted at founders who are first-time managers and the example is managing a new engineer, but you could apply most of this at different levels of scale and to different job functions.

Here’s the outline:

1. Great management starts with great hiring

2. Use onboarding to set up new folks for success

3. There are four types of conversations

4. Give feedback early and often, in private

5. Think about how to motivate and inspire your team - and do it

6. Show care, have boundaries

7. Part ways gracefully

Great management starts with great hiring

Hiring could easily have it’s own book, but I’ll share a few key things to think about during this phase of the management process:

1. Hire people who align with your startup culture. Think through the key attributes your existing team has in common and whether you think someone could thrive in your company without each of those. And then make that the bar for hiring. For example, if you work long hours in the office and expect employees to as well, be upfront about that. And don’t hire people who can’t match you if that’s a non-negotiable.

2. Have two forms of your job description during the hiring process. One form is the publicly advertised description. It should be specific, clear, and concise to bring in as many candidates at the top of the funnel as possible. The level of detail here is the headline responsibilities so candidates can get a sense for the role. And then you should have a more detailed job description that’s shared during the interview process which has the sub-bullets under those - what are examples of the specific tasks the person will be expected to do; what are the absolute must-haves vs the nice-to-haves. You should have a conversation around this during the interview process to make sure there’s alignment. The detailed job description is what you’ll be holding them accountable to if they take the job; it can and will evolve over time as your startup’s needs change, but there should always be 100% clarity and alignment as to what is.

3. Have a clear and consistent compensation philosophy that you apply fairly across employees. Startups can rarely pay top dollar for talent, but you should have a way to communicate this to employees and compensate them holistically in a way that feels good to them - both relative to their other opportunities, and relative to other employees in your company. For example, some startups aim to pay in the 50th percentile on cash but 90th percentile on equity according to Pitchbook comps for the role, level, and company stage. If you can explain that philosophy and stick to it, it will help employees feel they are paid fairly. You must apply this evenly and not allow substantial wiggle room for negotiation, or you’ll end up underpaying certain groups of people, and they may find out later. As a woman, I’ve been on the other side of that earlier in my career, and it sucks; knowing you are underpaid becomes a massive distraction when it should be something that you don’t have to think about.

Use onboarding to set up new folks for success

The first day someone joins your company, you should give them an onboarding doc that covers the following things:

1. Key software they need to onboard to, including what your team uses it for and how to log in.

2. Key context documents for their role. For engineers that might include product docs / PRDs, the roadmap, how to access design files, key eng documentation, links to sprint planning, docs or articles to help them ramp on your industry and acronyms, etc.

3. List of who’s on the team and what they do. If you are a small team, they should set up 1:1s with everyone in their first week.

4. The longer form job description (the 2nd doc from above). Bonus points if you can add clarity as to what “meeting expectations” and “exceeding expectations” would be for their primary job responsibilities.

5. A list of early projects and the context they need to ramp up on those. Include clarity on priority, timeline, how long you expect it to take, and who to go to to get help with it. Make sure the first few projects are “easy wins”. If it’s an engineer, they shouldn’t be struggling for their first two weeks to ship their first thing. Help them build momentum by giving them a few easier projects they will definitely succeed at so they can learn the code base and start to build relationships on the team before they do something hard. Once they have relationships on the team, it will feel easier to ask for help if they get stuck on something harder.

There are (at least) four types of conversations

There are at least four types of conversations you can have with direct reports, and each one requires a different cadence and approach. Not every one requires a meeting, but some do.

1. Prioritization conversations

2. Status updates

3. Brainstorming / problem solving / open-ended discussion

4. Professional development / feedback / growth

If you are a small team, you can likely address prioritization and status updates during a daily team standup. Early on, you want to make sure you’re on the same page as your team as to what’s the most important things for them to work on each day. Later, as you build trust and they become more senior, you may not need this frequency. You’ll also have a desire to know the status of the projects, and this is easily covered in a short daily standup as a team, so everyone is on the same page. The key thing here is that there should be some regularly scheduled time on the calendar for these things - daily, every other day, or weekly depending on your team structure and pace.

Brainstorming, problem solving, and open-ended discussions are better handled as one-off ad hoc meetings, scheduled as the need arises. If a status update during standup reveals a kink in the product plan and a longer discussion is needed, schedule that time later in the day or immediately after standup for the folks who are relevant, and don’t drag standup out for everyone else. If you’re working on a new product plan and want team feedback, schedule time for that. To the extent possible, batch meetings together so that you are not leaving engineers with awkward 30 minute gaps between meetings.

Lastly, professional development and feedback should be a separate regularly scheduled conversation delivered 1:1. More below.

Give feedback early and often, in private

This one seems obvious, and yet most new managers don’t do this well. Giving constructive feedback is uncomfortable and it takes time to get better at it. Here are some tips:

1. All constructive feedback should be delivered in 1:1 sessions. For some people (myself included), we haven’t gotten a lot of constructive feedback in our lives, and it can activate the fight-or-flight part of our brains, which shuts off the rational part of our brains. We can’t actually process and respond to feedback in that fight-or-flight state. This is why you want to create as much psychological safety as possible. Hearing something you didn’t do well can be scary in a 1:1 setting; it can feel especially bad if your colleagues are around to witness it.

2. Set up regularly recurring 1:1s for feedback, coaching, and professional development related topics with each person on your team. I’ve found that every 3-4 weeks is the right cadence for this. If you don’t have a separate conversation scheduled, it will never be the thing you prioritize talking about because it can be the most uncomfortable. You will spend 1:1s on status updates and other more “urgent” topics, but never cover these important ones. Topics can include:

   1. Feedback on recent projects - including highlighting things gone well as well as things that didn’t meet expectations. It’s particularly important to highlight things going well and celebrate those.

   2. Any minor issues that arose since the last conversation. Typically I’ll wait until minor issues occur twice to point to a pattern, but sometimes something happening once is enough to bring it into a conversation. Approach with curiosity and assume good intent. Ask questions to understand the context. And be clear that the thing you are bringing up is a concern.

   3. Reviewing the detailed job description and sharing how you think things are going relative to expectations. This is particularly important if things aren’t going well. Start this conversation early and document it. Align feedback to the expectations of the role. Make it clear if the employee is not meeting expectations.

   4. Discussing career goals and the evolution of your company. Even though there might not be a lot of degrees of freedom for what your employees can work on in the early stage, if you know what their goals are long-term, you can start to set them up in that direction. E.g., if an engineer wants to become an engineering manager but the team is too small right now to justify it, you can give them tech leadership opportunities to start to build those skills. People appreciate this type of long-term thinking because it shows you are invested in them and their career.

3. Ad-hoc feedback should be offered with care and thought. Some people want to know the moment they did something well or not well. Other people would rather it be delivered in times when they can know what’s coming (e.g., scheduled 1:1s). Learn how your employees prefer to receive feedback, and try to offer it to them in the way that feels best for them so it can be better received.

Think about how to motivate and inspire your team - and do it

There are many ways to motivate and inspire a team, but ultimately this is something you’re going to need to discover what works for you and your team. There’s a broad menu of options here, choose what feels authentic to you:

1. Compensation - e.g., bonuses, equity, etc. This is not my preferred form of motivation because I think it’s short lived. People feel great when they get a bonus, but with the exception of sales teams, this tends to be short-lived and irregular. I’d rather focus on sources of motivation that are deeper.

2. Connect your team to the customer. Bring folks who wouldn’t normally attend user conversations into them. Bring quotes back from user feedback for the team. Bring your customers into your office for lunch. The human element of wanting to help people is so universal; getting to be directly in touch with your customer can be very motivating for folks.

3. Hire people who are motivated by your mission and help them stay connected to it. If you are a mission-driven company, use this as a strength. Bring people onto the team who inherently care about what you do, and each time you do a planning cycle, help the team re-connect to the mission and their reason for being there.

4. Give people hard problems to work on at their edge of growth. Challenging, interesting work can be extremely motivating to some people. When people are learning and growing (vs. bored), they tend to be more engaged. Keep this in mind when hiring and staffing projects.

5. Celebrate wins publicly. At the all-hands. In slack. In weekly team meetings. In 1:1s. Startups are so focused on solving problems, we forget to celebrate what’s going right. Hit a goal? Celebrate it! Won a new big customer? Celebrate it! Shipped a new product? Celebrate! Anything from calling it out publicly with appreciation to an actual celebration event can work. Just don’t forget to do it.

6. Bring the team together to bond. Offsites, happy hours, lunches. Anything to build connection across the team. Help them know each other as people. This is especially important for remote teams.

Show care, have boundaries

There’s a delicate balance between getting to know your team as people and caring about them, and maintaining professional boundaries. A few ways to show care:

1. Ask about how their weekend was, their vacation, etc.

2. If you know a family member is sick or having a hard time, check in.

3. If they tell you something in their life they are excited about is happening, ask them how it was after.

As you get to know them and show care, you also want to keep in mind you aren’t aiming for close friendship. Why? You need to be able to fire your employees. And it’s really hard to fire a good friend.

You’ve gone too far when:

1. They are telling you intimate details about their romantic life

2. They are sharing information with you that is better shared with a partner or best friend and not important for you to know for work

Keep it professional and have boundaries. If they start to share information that you think is past reasonable professional boundaries, let them know that with care.

Part ways gracefully

Gosh, I wish we never had to fire people. Because no founder has ever said “wow, firing is my favorite part of this job.” And yet I’ve heard from so many founders “I wish I had done that sooner.”

How to part ways gracefully:

1. Be really clear about expectations up front and deliver feedback early and often if the employee is not meeting expectations.

2. Document, document, document. If you see someone headed on a path where you might need to fire them if it continues, then when you give them feedback, make a record of it in your private notes. During and after conversations, share a written down bulleted list of expectations for their role and where they are relative to those expectations - make sure they have a copy and you keep a copy.

3. Show care along the whole journey. Be really curious about what’s going on for them that’s getting in the way of them meeting expectations. Be understanding, but don’t waiver from what the expectations are.

4. If you can do all of this well, you might find employees choose to leave on their own accord because they realize they cannot meet the expectations for the role. Gold star if this happens, but you shouldn’t wait for it to.

5. Let someone go if they are consistently not meeting expectations, and don’t drag this out. Keeping someone around who isn’t working out is an energetic weight on the team much bigger than you even realize.

Final thoughts

I think of management as a craft the way that engineering or product design is a craft. Most people can figure them out to some basic level on their own by doing online research. But just like newer engineers and product designers benefit tremendously from someone with more experience reviewing their work and explaining feedback to them to improve it, managers also benefit from this type of apprentice-like mentorship. Startup founders often don’t have the benefit of someone to be their mentor as they step into management for the first time; seek out folks with management experience in a startup that you resonate with to learn from (whether in a formal capacity as a coach or advisor, or an informal capacity as a mentor).

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*Of course this isn’t universally true across all of tech. There are great managers in all sorts of places. But the industry as a whole seems to under index heavily on management as a craft.