Being a manager is rewarding, but it can also be isolating.
The higher you rise through the ranks of leadership, the fewer people you can turn to and ask, “Am I doing it right?”
That’s why it’s so important to occasionally compare notes with other managers in order to learn new ideas, get a glimpse of other company cultures, and simply commiserate with people who are faced with the same choices as you. In that spirit, we reached out to managers and former managers from the startup world for their own experiences leading teams.
Whether you’re also managing a startup or you’re working in a company with a more stable hierarchy, you’re sure to learn something about what great managers do from the insightful and deeply personal anecdotes these successful managers have graciously shared.
How great managers communicate and instill company values
Getting your team aligned behind the values of the company is one of the things that separates great leaders from average managers. When the people you serve cannot just believe in your company values but can also embody them on a day-to-day basis, it makes your job as a manager a magnitude easier.
“‘Repetition never ruins the prayer.’ As soon as you feel like you’ve said it too much, it’s probably just sinking in.”— Margaret Kelsey, Marketing Director
“By defining what values they believe matter and why (ideally, that includes capturing and reflecting the values of the team you work with and what they believe matters). By leading by example. By repeating, like a steady drumbeat, in the background on an ongoing basis. By adapting when some aren’t working and showing you’re listening and reacting. And by honestly caring about instilling the right values, not on being right.”— Suneet Bhatt, Boldr Impact, Right Question Institute, and Dream Village
“First they live them themselves. They make sure the values are just baked into how they give feedback. How they organize work. It shouldn’t be a voice from on high: ‘Do this thing!’ It should just be a natural extension of how they work, hire, train, evaluate, etc.”— Diana Potter, Qwilr
“1. Hire for your team with your core values in mind above all else (and have a strong hiring process around it). Values are only impactful or useful if they are not just words on your website but living and breathing through your team. Skills can be taught, core belief systems cannot.— Bee Strydom, Hotjar
2. Repetition. I like this quote by Jeff Weiner (CEO LinkedIn): ‘When you are tired of saying it, people are starting to hear it.’”
As you may have noticed, the most commonly repeated theme of these answers was . . . repetition itself! Committing to repetition can be a challenge for managers, because no one wants to sound like a broken record.
But great managers have the confidence and the discipline to work like a symphony conductor running their musicians through the same tough passage of music until it’s perfect.
As a manager, you impart values through repetition by returning to the same themes in meeting after meeting and then connecting your choices to those values. If you’re setting aggressive deadlines, for example, don’t explain it in terms of “increasing efficiency,” but in terms of “putting our customers first.”
In one-to-ones, you should also practice values through repetition by focusing on some core company values each employee can focus on for a given month. Return to these values again and again and relate them back to day-to-day work. Eventually, those values will become an integral part of how your team members think about work, instead of just empty slogans.
How great managers communicate praise and/or criticism
Praise and constructive criticism are the two most basic tools every manager has to work with. Yet learning when and how much of each to dole out can be a challenge. Effective managers know how to deliver both types of feedback in ways that not only motivate the individual being singled out, but the entire team.
“We celebrate praise via email, in one-on-ones, and in public channels. We’re also highly specific in that praise to help make sure someone knows the why behind the praise. And we do the same with constructive feedback and coaching—except that’s done on an individual basis.”— Leo Strupczewski, Curalate
“I think a good rule is generally ‘praise feedback in public, critical feedback in private.’ The Radical Candor framework is great, where feedback is delivered in the right way, motivated by absolute care and trust and ideally as quickly as possible, so that there are never any ‘surprises,’ good or bad, down the line.“— Bee Strydom
“Depends on the person. Criticism is private, always, and happens in one-on-ones typically. Praise is a mix of public and private. One thing I personally ask my team when they start is about praise. I’ve worked with people who cringe at public praise, so I ramp it down, and others who shine, and I ramp it up. But I still try and find a balance so, publicly, it’s not like one person seems to be doing way better because someone else doesn’t get as much public praise. Always a challenge!”— Diana Potter
“Largely in one-on-ones, although they will occasionally call attention to great work in Slack or the team meeting. More broadly, I think many managers would benefit from giving more specific praise. A lot of praise tends to be ‘nice work on that.’— Benyamin Elias, Content Marketing Manager ActiveCampaign
It’s more meaningful (and leads to better work) when praise is detailed, e.g., ‘I thought you did a really good job of pulling together background research to present to the team, then answering follow-up questions to get everyone bought in. I really like XYZ data point in particular.’“
“Praise publicly. Punish privately. At work. At home. Everywhere you exist.”— Suneet Bhatt
Most managers agreed that, for the most part, criticism should take place on private channels, whereas praise is more appropriate to public channels. That’s a fairly straightforward concept, since criticizing your employees in public settings can be demoralizing for the whole team, whereas praising in public is motivating and unifying.
Several managers mentioned an added element to issuing feedback, though: that praise and criticism should be tailored to what works for each individual. Some team members will inevitably be highly motivated by both praise and criticism, and a sprinkle of either will get you big results. But other employees will be indifferent to praise, and still others can find being singled out in public embarrassing. That’s why we recommend asking new hires about their preferences early in the onboarding process, so you’ll know what makes each employee tick.
How often do managers in your organization have one-on-one meetings with employees, and what is discussed in those meetings?
If praise and criticism are a manager’s primary ingredients, then one-on-one meetingsare the oven where they cook. More than any other form of professional interaction, one-on-ones are a chance to develop personal relationships with team members, have meaningful (and sometimes difficult) conversations, and collaborate on setting priorities for each individual.
How you choose to structure these meetings will directly shape your employee’s performance and priorities throughout their workweek, so it’s important to give them careful consideration.
“I have one-on-ones with my team and with my own lead every week. The purpose of these 1:1s? Continuous coaching and feedback on performance and growth. The idea is that this is your team members’ time; they set the agenda, they talk about what they want to talk about, whether it be personal or work, it does not matter. If there is a work issue that is causing pain or blockage, talking about it in this scenario is often necessary and alleviates anxiety. It’s a great place to be vulnerable too, both sides, and to build trust with transparency.“— Bee Strydom
Every other week for 30 minutes. Different managers run these meetings differently. It seems as though the most effective managers let their direct reports set the agenda, then contribute one or two bigger-picture ideas on their own (since reports tend to focus on the tactical, short-term stuff when left to their own devices).— Benyamin Elias
Weekly, mostly, but one-on-ones are really for the direct report to use for what they need: career coaching, interpersonal conflict resolution, metrics deep dives, etc. They should rarely be used for the manager’s agenda.— Margaret Kelsey
Every month. Usually, they’re used for evaluation but they shouldn’t be. They should be a safe space for employees to be vulnerable and get the guidance and support they need to make measurable progress and build accountability to themselves.— Andra Zaharia, former CMO and content team manager in two startups
“We have one-on-ones every week, and it’s one of the most important elements of what I feel like is a culture of healthy management at Clearbit. Before we meet, I’ll have written up an update in advance of our team meeting on what’s been good and bad in regards to progress on OKRs. So, sometimes that’ll bring up a few points of discussion. We’ll go over any issues that have come up from the past week and take a look at the week ahead — not as status updates, but to make sure the path to progress is as clear as possible. I’ll also bring up any questions or concerns that have been on my mind. We wrap up every one-on-one with some two-way feedback (me to my manager and vice versa). This, too, has been written up in advance of the meeting, and we use the in-person time to discuss the feedback.“— Janet Choi, Clearbit
Managers reported a wide range of variation in the frequency of one-on-ones, as well as the balance of short and long-term goals discussed. However, most agreed on the importance of letting an employee help set the agenda for these meetings. While it’s appropriate to allocate some time to discussing the issues of the day, it’s even more important to use one-on-ones to have the kinds of conversations you couldn’t have anywhere else. That can mean discussing workplace anxieties, helping an employee plan their career trajectory, and exchanging feedback.
Allowing for that kind of vulnerability and spontaneity requires that managers approach these meetings with a certain amount of looseness instead of tight control. But that’s not to say that managers shouldn’t have some basic templates on hand to guide the conversation and draw out an employee’s honesty.
On the contrary, being prepared, and discussing what topics you plan to cover in a given meeting is important to getting the most out of this critical time.
What makes a manager a “startup manager?” How does a manager in a startup balance the need for growth with maintaining good relationships with their team?
Startups are arguably the most challenging environments for managers because leaders must hold a team together in an atmosphere where roles, duties, and scale are rapidly evolving. On the other hand, the dynamic nature of startups makes them ideal laboratories for managers to experiment, which is why these managers have such diverse and compelling insights.
“A startup manager is someone who is willing to dive into the work with his or her reports. He or she seeks to guide first and provide the autonomy that startups require, but they’re never above doing the hard work—to better understand the problem, the workflow, or the opportunity and to build empathy with a team. Startups are hard work, and a manager needs to display the willingness to do that. It goes a long way in getting buy-in from the team.”— Leo Strupczewski
“I think of folks as on a spectrum of ‘shipper’ to ‘polisher.’ It’s good to have a good mix of folks from the spectrum on your team, but as a manager, it’s important to encourage the “polishers” to ship earlier than they might be comfortable with, and likewise encourage the “shippers” to slow down and QA their work. Encourage, but don’t try to swap them to the other side of the spectrum.”— Margaret Kelsey
“They can handle the craziness and bring balance for their team. They know how to champion people around an idea and push for amazing things at startup speeds. They also know when to remind people to take a holiday or just work less, because no one benefits if they burn themselves out. A good startup manager doesn’t encourage 80 hour weeks and does encourage brilliance in balance. They should also be a bit more hands-off. Part of the enjoyment of a startup is building something from nothing, and that takes autonomy and trust. Micromanagers need not apply.”— Diana Potter
“Startup managers (or managers at fast-scaling companies) have to deal with more uncertainty and change. A process established today might change in 6 weeks or 6 months as the priorities of the business change. Uncertainty is stressful for managers and reports. A manager can help their reports by hearing them out and getting their perspective on projects as they change. People are more invested in work that they’ve had a part in shaping.”— Benyamin Elias
“1. Transparency—confess when you make mistakes, encourage people to talk about how they are feeling. Rapid growth can be scary.— Bee Strydom
2. Be prepared to ‘give away your job’ so you can continue building.
3. Collaborate and listen: Startups are exciting but hard work—a roller coaster of emotions and events. Many people wear many different hats, and the need to support them as they do so is crucial.
4. Show up for your team in two ways: a.) Listen to them, don’t just focus on their work; get to know them outside of their work. b.) And of course, champion for them. Give them projects that challenge them, give them feedback that helps them grow, and stick up for them when you feel you need to.
5. Embrace uncertainty—in a big way!
6. Prioritize: You have a role that likely requires you to both manage and make your own individual contributions, which can be a serious challenge. Higher-level, team, and personal goals can be great drivers for deciding that prioritization.“
A handful of managers replied that they don’t believe there is a difference between managing at a startup and anywhere else. Among the other managers, however, there was a general consensus that managing at a startup means allowing reports to work autonomously whenever possible, so they feel genuinely invested in work that is often challenging and hectic.
We’ve written before about how challenging it can be for some managers to step back and delegate, but as these managers make clear, extending trust and allowing for independent decision-making is crucial for team members to feel truly invested in their work.
The other major theme we see here is offering support to your team, but recognizing that support can take different forms at different times. As one manager mentioned, you’ll have to challenge some team members to step up, and you’ll have to help others slow down, depending on their particular quirks.
It’s important to go about giving this support in a structured way and tracking each individual’s needs over time. To be able to spot patterns and record your reactions to them, you need to keep records of your interactions with employees in one-on-ones, ideally using a platform like Uptick.
What is the most helpful thing a manager has ever done for you?
The easiest way to remind yourself that your work as a manager is important is to remember the managers and mentors who were important to you. To remember the great managers who invested their time and energy into helping you grow is to remember that you have the ability to be the same powerful force in the lives of your team members.
“Reminded me that my empathy and sensitivity are strengths for connecting with people.”— Margaret Kelsey
“I had a manager once say, ‘I’ve seen you do better than this.’ He was right. He had seen me do better than that. I don’t think this would have worked without an established, high-trust relationship—but, in this case, it’s what I needed to hear.”— Benyamin Elias
“Setting ambitious yet motivating goals using a personal development framework.”— Emil Kristensen Sleeknote.com
“1. Trust from day zero. It has been critical to my success.— Bee Strydom
2. Let me lead the way for my team and department.
3. Confidence. I have a solid sense of self-competence but sometimes struggle to relate that in a multi-person meeting setup. Having your lead be a mentor, an advocate, and cheerleader, someone who is on your side at all times, is irreplaceable and does more for your career than can be first imagined.
4. Lastly, and most importantly, care. He personally really does care about me as his teammate, as a human. This means more than any promotion, any pay raise, and any bonus.“
“I’m lucky that I’ve had three great managers in my career so far. The common element they shared in their management style was giving me the autonomy to work while using one-on-ones and check-in sessions to guide my problem-solving. Common questions they’ve all asked is, ‘Why?’ or ‘How so?’ and then constantly repeating that question until they’ve guided me in finding the answer. Sometimes, that’s a painful process. Other times, it’s relatively quick. But, each time, it’s helped me build the muscle memory to do it on my own when I find myself stuck.”— Leo Strupczewski
“Cared.“— Suneet Bhatt
Nearly every response to this question could be boiled down into two words: trust and care. Trust, in this context, means trusting charges to make their own ways as leaders, to succeed using their own personalities, and to figure out the solutions to problems without being spoon-fed the answers. And that trust is built on a foundation of care.
These managers aren’t describing mentors who constantly patted them on the back, but people who built meaningful and profoundly personal relationships with them. These managers proved their personal investment in their reports, and it enabled them to have difficult conversations that actually pushed their employees further.
That should serve as a reminder to every manager: our workplace relationships are real relationships, and just like in every other facet of our lives, we get out what we put into them.
Great Managers Lead from the Heart
So what have we learned here?
If nothing else, that being a startup manager is a challenging role, since you have to be both a source of stability and a very agile member of your team. You have to be consistent in modeling your values and proving your loyalty to your team. At the same time, you have to know when to challenge your reports and when to buoy their spirits; when to get in the trenches with them and when to give them the reins.
These are always going to be challenging choices, and five great managers might have five different approaches for facing them. Yet, despite differences in style and method, each of the managers who shared their insights here has a common philosophy with Uptick: management is about relationships.
The fundamental thing that all great managers do is build a practice of cultivating and nurturing those relationships every day of their working lives.