8 Ways to Retain Top Employees

And if you’re a founder, you’re the leader of the team.

But your strongest team members also hold the team together.

If they leave there’s often a massive hole, not just in terms of output, productivity, and creative thinking but also morale and culture.

I’ve led employees through crises and lost some great ones too.

This week I’m sharing the playbook for how to retain your top performers.

8 Ways to Retain Top Employees

Align on Expectations Before They Start

Joining a new company is a risk. Any employee you hire will be ruthlessly evaluating you and the decision they just made on Day 1 (and indefinitely into the future).

Harvard Business Review says that 17% of new hires quit within their first 3 months.

Why do people leave jobs so quickly?

They were sold something different than what they received.

Be candid in your interviews and any onboarding materials you give them.

When I joined Airbnb I knew right away it wasn’t the right fit for me:

• My first manager told me in our first 1:1 that he was “excited to build trust with me”, I was coming from Uber, where the assumption was you were competent and trusted if you passed the interview process.

• In my first week other team members joked that placement for selection into our Airbnb Plus program should primarily go to hosts living in “blue states”, I firmly believe decisions like that should be made on merit.

• The data science org, which I initially joined, wasn’t empowered to help drive product decisions or run experiments like they were at Uber, I transitioned to Product Manager shortly after.

Perhaps I was naive or didn’t ask the right questions during the interview process, but it’s the job of the interviewers (or, in the case of a startup, the founder) to correctly set those expectations before a candidate leaves their job and signs on to join.

Understand & Manage Your Team

If you wanted to be a “manager” you would be working in big tech, but managing is part of the job of a founder.

And you can read all the management advice you want (this talk by Ben Horowitz is one of my favorites) but you’ll be better off developing your individual style. It’s not one size fits all.

For example, I like to be ”in the details” as Brian Chesky says and am entirely focused on output async, but very jovial when I’m in person. That works for me almost all of the time but that may not work for your personality.

More importantly, understand the people you’re managing.

Management is a weird non-competitive and one-sided game of poker, doing well is more determined by how well you can read and understand the current feelings, desires, and tendencies of the people you’re with than anything to do with you.

Take Feedback as Well as You Give It

The buck stops with the founder. You should be a sponge for feedback and seek it out from your team.

They will follow your lead on this. If you’re not interested in their thoughts, they’ll care less about yours.

No one wants a manager or leader who gives tons of feedback but isn’t willing to change, or at least earnestly listen, themselves.

Leave Them Better Than You Found Them

Invest in your own success by giving your team what they need.

Don’t just hand out anything they ask for, make them make a case for why a tool will be useful and genuinely evaluate its merits as best you can, but don’t handicap them if it genuinely is the right solution for the business.

This mindset should usually gets applied to SaaS tools, laptops, etc. but you should extend it to upskilling.

I’ll always be thankful to Uber for investing in having me learn how to build machine learning models back in 2017.

I was able to apply what I learned to help improve various parts of our user and driver pricing but, maybe more importantly, it made the decision to eventually leave incredibly hard because I knew they believed deeply in me.

Develop Rituals

If you’ve ever worked in a company with a full sales team you’re probably familiar with the idea of someone “ringing the gong” when they close a sale.

It’s corny, and sometimes the product teams hate the distraction, but it’s a shared way of celebrating accomplishments that help the business.

Every startup’s culture will be different (lean into uniqueness) so find big and small rituals that fit the personality of your team.

For example, in my old startup Launch House’s early days Kim Kardashian mailed us a cake that was meant for Paris Hilton. After that, cakes became part of our lore and we would mail a cake to an employee on their birthday and do our best to have it arrive during a team meeting so that we could celebrate on Zoom.

Make Growth Plans

The best employees join startups to learn by doing and to grow faster than they could at a more stable, bigger company.

While this is your advantage in recruiting, it also requires you to stay on top of their growth while they’re working for you.

If they don’t feel like they’re getting the opportunities or level of work they expected then they will leave.

At the start of each quarter use one of your 1:1s to intentionally set a growth plan for the quarter that includes what’s highest priority for the business as well as the skills they want to acquire.

Caveat it with the universal truth that startups are chaotic and 3 months is a long time, priorities may change and you need them to prioritize what the business needs, but that you’ll make an effort to give them the types of opportunities you discuss.

If you’ve hired the right people then these goals should already align with what the business needs anyway.

Conduct “Stay” Interviews

You can probably sense if an employee is restless, demoralized, or thinking about leaving.

This is easier to do in person, where you can see their body language and how they interact with others on the team, but it’s possible remotely too by keenly observing their intonation and if they become less proactive.

Remotely I really like using some of the sentiment tracking features in read.ai for this. They’re the best AI meeting assistant I’ve tried (and I’ve tried a lot).

Ideally you have good enough relationships with your team where you get constant feedback on this and call pull them aside ad hoc if needed to dig into why they’re feeling down.

But specific 1:1s to learn their point of view about their role help force those conversations.

Don’t Make It a Family

Don’t ever let your team think of themselves as family, and don’t fall into that trap yourself either.

You will need to fire some of them.

You will need to deny them of things they want.

You will need to make decisions that go against their advice.

You won’t be able to share everything about the business with them.

If you set the expectation that you’ll prioritize their well being over the survival of the company, you’re setting yourself up for a very unfriendly conversation down the road (probably at an inconvenient time).

They are here because they can add value, not because you care about them.

You probably care about them too, but that isn’t why they’re here.