It’s a hard pill for any manager to swallow.
A high performer on your team that you’ve come to rely on announces they are leaving their role. As a manager, you’ve personally invested in this person’s growth and may find yourself tangled in a classic corporate conundrum: you were drawn to a high performer for their ambition, but their ambition has taken them down a new path — one away from your team.
Clarissa Shen has seen this trope play out at nearly every startup and team she’s worked on. A longtime startup operator and the current COO of the biotech company Q Bio, Shen’s seen companies that have scaled from just 15 people to over 800.
Shen knows that all startups have their fair share of growing pains, and the macro effects of growth are harder to see in the day-to-day weeds for managers of teams. But one of the most common obstacles managers run into is navigating when a high performer decides to move on. “It’s very hard to give up someone really valuable that you also depend on,” Shen says.
It often comes as a surprise, especially with managers who may have envisioned their team members moving up through the ranks at their company or even stepping into their own managerial shoes.
As much as it’s a surprise to hear that someone you’ve grown to trust is leaving, it’s even more surprising that managers are not prepared for it.
The experience happens so often that it catalyzed Shen to craft a new philosophy: Managers should always be prepared to give away their people, and when the time comes for a high performer to leave, Shen argues that managers will actually be better off for it.
Pulling from the ethos of Molly Graham’s blockbuster Review article “Give Away Your Legos,” Shen has architected her own framework for how managers can avoid being caught off guard when a high performer leaves, and instead learn how to proactively manage for it.
In this exclusive interview, Shen walks us through the overlooked and underappreciated benefits of high performers leaving a team or a company. She starts by unpacking a real-life scenario of high performers on her own team leaving, and what lessons she drew from the experience. She also unpacks the hidden benefits of how people leaving can actually help a manager’s career or a company’s reputation.
She also shares her tried-and-true tactics for getting direct reports to open up about their own career aspirations, and how this can help manage expectations for everyone on a team. She wraps up with tactics specifically for founders and executives on how to promote a culture of “giving away your people,” across an organization and why developing a reputation as a talent factory is one of the best free branding strategies a startup has at its disposal.
WHAT IT LOOKS LIKE TO GIVE AWAY YOUR PEOPLE
The first time Shen took on a manager role, she knew she had a star direct report on her team. This particular young woman was ambitious, driven, and was perfectly suited for the management track. Shen thought back to the high-impact managers she had in her past roles and wanted to pay forward the mentorship and advocacy they had imparted to her.
So Shen took a proactive route in making sure this young woman had all the tools she needed to be set up for success. In their one-on-ones, she took the time to identify the many strengths this direct report had, as well as opening up a conversation about an area she saw room for improvement.
“I knew that to take on a manager role at the company, a strong command of data analysis was critical,” Shen says. “So I pushed her to take on a tour of duty around analytics. Even though she was hesitant, she rose to the challenge, and I think it built up her own confidence.”
Shen was also feeling confident that she was inspiring her team to think bigger and championing new growth for the company. But then the unexpected happened.
“She told me that she was finally ready to apply for business school, and she would be leaving the company,” Shen says. “While ultimately I knew that move was right for her, I was still surprised — I didn’t even know she was looking to get an MBA.”
Shen realized that, while she was on the right track with how she proactively managed her direct report’s growth at the company, she was missing a big piece of the puzzle. What she failed to do in their weekly 1:1s and quarterly growth conversations was drill down and get specific on what her direct report saw as visions of success — beyond the walls (or Zooms) of the company.
“One thing I learned early on was managers need to have very specific conversations with reports on what they are looking for in their next growth opportunities,” Shen says.
Accept that people are going to leave. Especially if you are a first-time manager, it’s much easier to go into the role accepting that someone is going to leave, rather than blame yourself for when it happens.
THE HIDDEN BENEFITS OF ‘GIVING AWAY YOUR PEOPLE’
But learning to ‘give away your people’ doesn’t end with preparing for the day it happens. While it may feel counterintuitive, Shen says the best managers and founders actively push their people to take on new challenges, which might mean leaving.
“Why hold people back?” Shen asks. “If you do, you are just creating tension in a different way. Giving away people is giving away power in some cases. I fully recognize that can be really hard. But I’ve seen it pay off both long term within the company as a brand builder for someone who develops these people, but also as a tool to build a reputational brand outside the company.”
To help illustrate this point, Shen provides two likely scenarios of what can happen once someone you manage decides to take the next step in their career.
A high performer joins a new team within the organization.
Rather than treat a direct report leaving for a different team as a personal loss, managers should realize that this can, in fact, be a tremendous asset, especially if they’ve formed a good relationship with this person. “They can become a peer to you, and continue advocating for you and your team inside the org,” Shen says.
And from a founder's perspective, a high performer in one area leaving for a different area of your company (that you maybe did not imagine them in) can be a huge benefit because of the institutional knowledge they are carrying with them into their new role.
“People with institutional knowledge in different areas strengthen the bridges between disparate functions, which can be really important for early-stage startups,” Shen says. “The collaboration long-term has compounding benefits.”
Politics is sometimes a dirty word. But enabling people to have their own ambitions is good politics. It’s bridge-building for individual managers as well as the organization.
A high performer leaves the organization to go somewhere else
Someone on your team gets a job somewhere new? Instead of fretting about all the scrambling you’ll have to do to fill that person’s shoes, start thinking about the move in terms of your own career. “I think it helps managers to think about the long-term benefits of a high performer on their team leaving,” Shen says. “We have to be a little bit selfish about it too, from an incentive standpoint.”
“As a manager that promotes ambition and encourages growth, you just helped someone get their next job,” Shen says. “In the short term, this can be very painful. But in the long term, that is the network you are building. You may be giving up power in some way, but you are building an even more powerful bridge for the future.”
And founders should also consider the reputational benefits that result from a talented employee leaving their startup for somewhere new.
When enough great talent has your startup’s name on their resume, you get known as a place where strong performers come from. This is part of brand building and will help with recruiting in the long-term.
“Great talent that comes from your startup is a broader sign of success beyond company financials,” Shen says. “It signals that there is innovation and wealth creation in your network. I like to think of this as part of stakeholder value creation and not just shareholder value creation.”
THE MANAGER’S PLAYBOOK TO GIVING AWAY THEIR PEOPLE
To help get into the habit of ‘giving away your people,’ Shen outlines a few low-lift tactics that managers at any stage can start implementing into their routine now to inspire their team to think about their own long-term growth.
Put it on the calendar
Most managers already have some structured growth conversations in place. But while a bi-annual performance review may (technically) get the job done, it’s only the bare minimum.
The more time and space managers can carve out for their direct reports to reflect on their own growth, the stronger the relationship they are going to build. One simple way to do this as a manager is to set up a regular cadence of these kinds of growth-oriented meetings in the calendar. This is especially important for high performers where you want to invest extra time.
Shen shares a few tips on what can help boost this conversation from becoming “just another check-in” which quickly gets eaten up with a long list of to-dos and status checks in the midst of a fast-paced startup.
Try making every fourth 1:1 a career growth conversation. Block off at least an hour of time, allowing for the conversation to meander
Create a unique title for the meeting. It should be separate from a weekly 1:1 and a quarterly performance review
Come prepared to talk about your own career growth and bring examples or stories of opportunities that you’ve spotted for yourself
Beware of boxing people in
Shen warns of a common trap that managers fall into after watching a person on their team excel at one particular area again and again. That person can get boxed into one specific role, and overlooked when it comes to new projects to tackle.
“If you become the go-to person for something specific – all of a sudden, your plate is always full with the same set of challenges. But this doesn’t stretch you or build up your skillset for the long-term,” Shen says.
Managers should keep their ears perked for this — especially during more formal performance reviews. For a proactive tip, managers should consider writing down one project that’s outside their direct report’s comfort zone for them to work on.
“This is where the ‘give away your legos’ advice is great — because you don’t want someone to own an area only because they are comfortable in it. Their ambition is just going to flatten over time. Don’t wait, but rather continue to push that person to build their muscle of taking on new things.”
Start during the interview process
Practicing a culture of growth-positivity doesn’t just start once an employee is hired. Shen says there’s no harm in managing expectations early on — even as early as the interview process.
“I actually ask candidates in interviews what their aspirations are for the next two or three years,” Shen says.
But rather than using it as a tactic to filter out candidates, Shen is laying the track for future growth conversations, should the candidate come on board. “Asking about this in the interview process hopefully gives you some indication of what they want and can help you kick off your conversations in your very first one-on-one — rather than six months down the line.”
On the flip side of the coin — it can be dicey as a direct report to be vulnerable about your own career expectations with a manager.
Lots of factors are at play that could be preventing folks from being honest about what they truly want. Reports could be afraid to express their desire to join a different team, for example, because it could feel like they are offending their manager.
The entire exercise of asking someone to open up about what they really want involves a substantial level of trust. In order to get to the bottom of what their direct reports’ true career goals are, Shen says it’s up to the manager to be open and honest about their career goals as well.
“One thing I like to start with is where I’m currently feeling in my role, and growth opportunities I’ve outlined for myself, so my 1:1s don’t feel like the conversation is one-sided,” Shen says. “It’s all about modeling the behavior you want to see. Come with stories of how you personally have achieved career goals or taken on a new role.”
Making an environment where people feel comfortable talking about their career goals means you have to be comfortable talking about your own aspirations and ambitions, too.
Be an advocate
As you start to pick apart and learn what your direct report has set their sights on, creating a safe and comfortable environment to talk about growth is only part of the equation.
Shen argues that the best way to ‘give away your people’ is to advocate for your team — whether that means recommending them to an open role on a different team or dipping into your own personal networks to help foster strong professional relationships.
“One of my first hires at Udacity was someone who I really relied on for executing and they helped to source and grow opportunities within our own team. We had a missing leadership spot on the product side, and I recommended him for it,” Shen says.
“It left a big gap in my business development function – but by ‘giving up’ that person on my team, I helped another part of the business grow and gained a strong partner that inherently understood the needs of my team. That was an experience whereby actively giving someone away, I saw the longer-term upsides for everyone involved.”
CREATING A CULTURE OF GIVING AWAY YOUR PEOPLE
Shen acknowledges that at the earliest stages of company building, putting in processes for developing team culture and career ladders is likely the furthest thing from a founder’s mind. But when the time comes that the organization does start to grow its headcount, Shen urges founders to act quickly and carefully here.
“In early-stage startups, there’s a tendency to fight growth and scale,” Shen says. “Founders sometimes want to stay flat as long as possible, because if they scale, it means they have to delegate leadership.”
It’s natural to feel anxiety around giving up control, especially as a founder that has built the company from the ground up. But Shen offers an alternative approach to how founders can view scaling up their people.
“Embrace the fact that you’re not always going to be a flat organization. Celebrate that moment when you realize that you will have your first people managers, who will bring different approaches to their 1:1s, documentation, and conducting performance reviews.”
But letting go of managing duties doesn’t mean founders and leadership teams don’t have any influence over how the rest of the company is managed. Like nearly all aspects of company culture, giving away your people is a top-down practice that ultimately needs to come from the founders.
On top of her duties as COO, Shen is an investor and a board member of several startups. When Shen sits down with founders to hammer out the first details of their people management processes, she never starts with a prescription for a problem. Instead, she starts with these question prompts:
What does the organization look like right now from a people management standpoint?
What conversations have you had with your people managers about how they’re thinking of scaling their own team?
Have you asked your people managers if managing people is something they enjoy doing?
Once the architecture of the people management culture at the company is ironed out, then founders can start to think about how they want to manage growth conversations. “Remember that scaling on a day-to-day basis starts with the people you have, and your people managers have the most influence over building and scaling the team,” she says.
Here are two methods that Shen has used in the past with her first people managers to implement a culture of giving away your people.
Invest in an executive coach
Particularly at early-stage companies, where the team is focused on finding product-market fit and building up the core company foundation, management usually falls on the backburner, leaving folks to just figure it out all by themselves.
But de-prioritize good management hygiene for too long, and many of the cracks that emerge as a startup scales will trace back to management training — or a lack thereof.
“In startups, there’s typically no structured training program for managing people. Employees know they aren’t going to be part of a well-known manager training program,” Shen says. “But that’s not an excuse for not investing in your first people managers.”
The biggest mistake I learned the hard way was not investing in my people managers early enough.
One way Shen has invested in her people managers is by bringing in an executive coach to work with all employees as soon as they take on a managing role at the company.
“If you set aside time with a coach on a regular basis, it’s a forcing function for managers to take a step back from day-to-day work and reflect on something else,” Shen says. “Usually a coach isn’t telling people what to do, rather it forces my managers to say what sort of soft skills they need to work on out loud,”
Even if these coaching sessions aren’t explicitly focused on managing when a high performer leaves, Shen says the goal is, in part, for managers to walk away with the communication and performance management skills that will assist them in that situation someday.
Set expectation documentation
To level-set here, founders need to codify the culture around career growth at the company. Shen calls this “expectation documentation.” Founders and execs need to be upfront about exactly what they want growth conversations to look like at their company and establish how often they should happen. It’s then on managers to execute. Here’s what expectation documentation can look like in practice:
Making time on the calendar. “On my team, we practice this by making every fourth 1:1 centered around the topic of professional growth,” Shen says. The cadence of these talks isn’t what’s important here, but it’s about establishing a baseline. “Sometimes it's just every quarter, some folks do every six months. But at least there is an established cadence that we agree on where we can mark this in the calendars as a longer 1:1 versus weekly check-ins that always get filled up, especially in a fast-growing startup.”
Adding it to the onboarding flow. “We have an onboarding checklist where I ask my people managers to set up one initial meeting to discuss career ambitions with every new hire. I also ask if they haven’t had one already to set it up with their existing people. The goal is to pass a positive, personal-growth culture down.”
Practicing regular check-ins beyond the first year. “I also ask that we practice the cadence of 30, 60, 90 and 120-day check-ins within a new hire’s first year, beyond just your standard performance reviews. The goal is to limit the number of surprises that may pop-up, and to give opportunities for employees to speak their mind.”
WRAPPING UP: LEAD WITH EMPATHY, ALWAYS
Founders can prepare their people managers with all the training in the world and managers can have growth conversations with their teammates every day of the week. But ultimately, when the day comes that someone exceptional is ready to leave the team, all that person will remember is how they were treated.
“There will always be tactics to try as a manager, but in the end, you have to think about how you make people feel. It won’t stick unless people feel like they’ve been respected. That’s ultimately what they will remember,” says Shen.
Cover image by Getty Images / twomeows