People Management for Rookies

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By Charlotte Dillon

Most people who start their own business do it because they have a great idea. Whether they’re setting out to start a new social media site or an environmentally-friendly sock distribution company, they do it because they’re excited about the business concept. People management is usually far from their minds.

It’s one of the least sexy parts of starting your own business. And it’s also the most important one to master.


In fact, people management is one of the things entrepreneurs struggle with the most, in part because it requires such a different skill set than other entrepreneurial qualities. But new entrepreneurs often make the mistake of dismissing it as a secondary task, instead focusing their efforts on what they think are more important duties.

Managing teams—especially remote teams—is hard, but really important. Poor prioritization leads to breakdowns in communication, which lead to mistakes in your team’s work, which spell out failure for your company.

The good news is, managing teams is a learnable skill. It boils down to a handful of daily processes that you can accomplish to be a competent and successful manager.

1. Be a Feedback Machine

First and foremost, your job is to help your team learn how to know what you’re asking of them. Whether that means helping them learn how to use your customer relationship management tool or tweak the tone of their client-facing emails, it’s important to give what researchers call one of the most important pillars of the learning process: feedback.

The problem is, a lot of managers view feedback totally backwards. Maybe they learned it from bad managers they had in the past, but these bad habits linger way longer than they should.

As it turns out, good feedback isn’t that hard to give—it’s something you can easily pick up on the job. If you want to teach your team how to be efficient, there are a couple steps you need to follow.

What to do

A recent University of Chicago study took a hard look at how managers give feedback, and came up with some surprising results. There are a lot of people who swear by only giving positive or negative feedback. But as the study shows, it’s a bit more nuanced than that. The kind of feedback you give your team really should correlate to their level of expertise.

It’s not just true at the workplace. It’s valid in all kinds of skill acquisition, from learning a new language to figuring out how to use a tool. As the study said,

“Across these domains, novices sought and responded to positive feedback, and experts sought and responded to negative feedback. We examine a motivational account for the shift in feedback: positive feedback increased novices’ commitment, and negative feedback increased experts’ sense that they were making insufficient progress.”

This should really impact the kind of feedback you give to your team. Here’s what new managers can from the study:

  • Use positive feedback to increase newbies’ commitment to the task at hand.
  • Use constructive feedback to help experts push past their plateaus.


Newbies and veterans will need totally different kinds of feedback

So let’s say you’ve just hired a new engineer. No matter how great your process is for onboarding engineers, there’s going to be a learning curve.

If your new hire deployed her first line of code, fire off a quick “good job” note, even if it’s not something you would note if a veteran team member had shipped. It doesn’t need to be a lengthy email—it can just be a quick line in Slack or a post in iDoneThis. This kind of positive reinforcement not only makes employees feel confident, it uses positive feedback to assure your new engineer that this is the kind of work expected of her, and will make her feel greater commitment to the job and your team.

Likewise, since experts respond better to negative feedback, don’t be afraid to send notes when their work isn’t up to snuff. So long as they still feel like an expert, and the intrinsic value that comes with their skill set, it’s okay to err on the side of a lot of criticism to get them motivated.

The study also touched on the importance of giving feedback regularly, but without micro-managing. Both novices and experts respond well to feedback given on a job that they feel is “finished,” rather than having a manager hover over them and interrupt their process. It’s especially important to establish the channels through which you give feedback.

  • Value their autonomy by giving feedback on finished projects, rather than interrupting employees at work.
  • Take notes on how things have changed after rounds of feedback. What kind of feedback worked? What didn’t?
  • Establish clear channels of communications where you give feedback, whether it’s email, a daily standup, or a tool like iDoneThis.

What to avoid

What if that new engineer isn’t doing a great job a month in? This is another snag new managers hit when they’re giving feedback. Giving constructive criticism is hard. But if you tiptoe around the real issues, you’re not going to be an effective boss.

Ayelet Fishbach, a professor of behavioral science and marketing at the University of Chicago, says that a major problem with constructive criticism is that we pay too much attention to the “constructive” side, and not enough to the “criticism.The problem, she writes, is that “negative feedback is often buried and not very specific.”

Of course, giving nitty-gritty feedback is time consuming and tricky. You’ve got a lot on your plate, do you really have time to get all you work done and give a lot of attention to all your employee’s work? Here’s a solution: try being a “do nothing” manager.

Being out and about amongst your team allows you to have a better idea of what’s going on, which means you can provide richer feedback that’s specific and grounded. As a manager, you need to:

  • Give specific, grounded feedback that’s based on assignments.
  • Avoid mixed messages. Don’t bury your critique in praise.

Fishbach’s research also indicates that it’s important not to “bury” your constructive points. That’s why it’s crucial to avoid the giving feedback in the form of a shit sandwich. You’ll just get disappointing results, with no one to blame but yourself.

As Tim Harford, journalist and author of Adapt: Why Success Always Starts With Failure states, “When we tell someone, ‘That was a great piece of work, there was just a small problem,’ what we tend to hear is, ‘That was a great piece of work.’ ”

Your feedback is totally lost.

So when your new engineer is making mistakes, your feedback needs to be really specific and have a clear message. What specifically was wrong with the project they just green-lighted? What should they do next time? If you want to praise something else they’ve been working on, save it for a separate email.

2. Schedule Regular 1:1s

A lot of people in the startup community swear by 1:1’s.

But a lot of managers get tripped up when it comes to actually implementing them. Is it supposed to be a quick coffee break with your team member? Or an hour-long performance review? While there’s no cut-and-dry formula for the perfect 1:1, there are certain steps you can implement to have really successful 1:1’s with your team.

What to do

First of all, it’s important to keep an agenda for your 1:1’s. The social-sharing tool Buffer has a rigid schedule for their 1:1’s:

  • 10 minutes to share and celebrate your achievements
  • 40 minutes to discuss your current top challenges
  • 10 minutes for the team lead to share some feedback
  • 10 minutes to give feedback to the team lead

But even if you only have time for a 20 minute meeting with team members, you should have a rigid agenda. It’s something Ben Horowitz, tech entrepreneur and co-founder of Andreessen Horowitz, subscribes to. In fact, Ben writes that the number one best practice of 1:1’s is to have the team members set the agenda.

“It makes clear that it is her meeting and will take as much or as little time as she needs. During the meeting, since it’s the employee’s meeting, the manager should do 10% of the talking and 90% of the listening.”


Your job is to ask questions and listen to your team. If they don’t have a lot of material they want to talk about, try asking some of these sample questions from Ben Horowitz:

  • If we could improve in any way, how would we do it?
  • What’s the No. 1 problem with our organization? Why?
  • What’s not fun about working here?
  • Who is really kicking ass in the company? Who do you admire?
  • If you were me, what changes would you make?
  • What don’t you like about the product?
  • What’s the biggest opportunity that we’re missing out on?
  • What are we not doing that we should be doing?
  • Are you happy working here?

As Horowitz’s questions indicate, 1:1s are a good time to get feedback about company culture. Even though we often think of company culture as ping pong tables or what the CEO decides about work-from-home policies or dress codes, it really boils down to your team members and what they do on a daily basis.

As Wistia CEO Chris Savage writes, company culture “is about everybody questioning their own individual decisions, and how those decisions shape the environment of the people around them. When everyone asks themselves how their actions affect the company culture, you create a positive feedback loop.”

What better time to get people to question their own decisions than in a 1:1?

What to avoid

One of the biggest mistakes managers initially make when coming into a 1:1 is having too much to say. Bad managers do the opposite of what Ben Horowitz suggests: they do 90% of the talking and 10% of the listening. The real problem with this approach to 1:1’s is that it removes the opportunity for your team members to reflect and think critically about their performance.

According to a Harvard Business School study, this is ridiculously important, and something that a lot of managers overlook. Reflecting on past work helps teams improves performance. As Joel Gascoigne, CEO and co-founder of the social-sharing tool Buffer says:

“I think a reason that the weekly or biweekly 1:1s can serve to accelerate progress at a startup, is that it is a deliberate and scheduled session to spend 10 minutes purely for celebrating achievements (something we often forget to be happy about and grateful for), and a lot of time to reflect and make adjustments.”

The “reflecting and making adjustments” aspect can be harder than celebrating achievements, since it’s not as black-and-white. It’s easy to look back on someone’s work and see what succeeded and what didn’t. It’s much harder to know how to fix it.

This is exactly why 1:1’s are so important. They’re a great time—potentially the only time—for you to talk to your team about big-picture items. On a day-to-day basis, you’re probably talking to your team about little things, like launching your new product, or polishing up pitch before your next VC meeting. It can be hard to find time to sit out and think, especially if you already know what you want to say.

So don’t talk through your 1:1’s.

  • To get the most out of 1:1s with your team, you need to encourage reflection, especially on past achievements.
  • Think of 1:1s as valuable opportunity to hear from your team members about what they’re reflecting on, and how everyone can perform at a higher level.

You might just learn something.

3. Overhaul Your Performance Reviews

Performance reviews are the bane of some employees’ existence. They’re dread-worthy, especially because at a lot of companies, your salary and rank depend upon how well they go.

On the other hand, people managers are often reluctant to throw out the handbook. Whether it’s a requirement from higher-up, or you’d like a regular meeting to review an employee’s performance, or you’d like the content of a performance review meeting without all the negative byproducts, there are a couple of ways to handle these meetings that won’t leave everyone with a bad taste in their mouth.

What to do

Performance reviews feel like the culmination of an important sum of time. But doing reviews on a regular, calendar basis can make people feel like everything is boiling down to that one moment, and that the rest of the stuff they do—on a day-to-day basis, goes unnoticed. The solution is to change both the content and the form of your performance reviews.

We spoke to a current Google and former Microsoft employee, who wrote about how frustrating performance reviews are for employees. One of the main problems at both Google and Microsoft, they anonymously stated, was that: “Celebrating performance through evaluation cycles (quarterly, semiannually, annually) creates a sense that every day work does not matter.”

In fact, a lot of companies are turning away from performance reviews altogether, including large corporations like Accenture. In the past five years, six percent of Fortune 500 companies have gotten rid of rankings, according to management research firm CEB. Starting in September, Accenture initiated a “more fluid system, in which employees receive timely feedback from their managers on an ongoing basis following assignments.”

CEO Pierre Nanterme says that the main difference is that they’re moving to a fluid model that measures daily progress. As he states,

Performance is an ongoing activity. It’s every day, after any client interaction or business interaction or corporate interaction. It’s much more fluid. People want to know on an ongoing basis, am I doing right? Am I moving in the right direction? Do you think I’m progressing? Nobody’s going to wait for an annual cycle to get that feedback. Now it’s all about instant performance management.

Of course, in order to move to a fluid model, the company needs to employ different tools. Instead of saving up evaluations and check-ins for once a year, they need to check in frequently with their managers to measure “instant performance management.”

This means a couple of things:

  • Use communication tools to help measure daily progress, like a daily standup, or iDoneThis. It’s important to take regular notes that document employee performance, or you’re going to forget about how they’re doing.
  • Check in with your team regularly about their performance, either in 1:1s or short performance evaluation meetings, rather than putting the pressure on a single annual meeting.

What to avoid

As software engineer and former Microsoft employee David Auerbach writes, the problem with ratings is when they’re attached to pay scale, they often make moving up in the ranks feel impossible.

“At Microsoft—it was the only path to advancement, so the company structure became more and more steeply vertical. Once or twice a year, we would all get together and decide how good each of our reports was, by ordering them from best to worst. The system was called the stack rank.”

Stack ranking is a performance review system that ranks employees against each other. Also referred to as “rank and yank”, stack rank creates a zero-sum management system in which one person’s positive ranking means another person’s loss. Critics point out that a process that creates inevitable losers and requires managers to fight on behalf of reports is unfair and disconnected from performance quality.

This is simply not what performance reviews should be used for. It shouldn’t feel like musical chairs when your team members step into your office—knowing that someone is going to get cut. It’s important to have a transparent structure, especially when it comes to promotion. When employees feel as though there’s potential for promotion in the next two years, they report much higher job satisfaction.

    • Don’t make ranking a zero-sum game—it won’t motivate your team.
    • Performance reviews should be about helping team members improve, not punishing them.

Performance reviews aren’t about slapping a grade on someone’s work. They’re about realistically analyzing what everyone’s strengths and weaknesses are, and thinking about how you can do better. But that’s not how a lot of managers use them. A lot of managers use them to berate employees for making mistakes, slacking off, or for cataloging all the ways in which they’ve failed this year.

Rather than waiting and hoping that their once a year performance review goes well, they’ll put effort into things on a day-to-day basis.

Bottom Line: Practice, Practice, Practice

Managing a team can be uncomfortable work. When a friend asked Ben Horowitz whether team leaders are born or made, he answered, “That’s kind of like asking if Jolly Ranchers are grown or made.” People management may feel as unnatural as red dye number 4, but it’s easy to learn. As Horowitz says, you just have to practice. A lot.

Some of these strategies, like 1:1s, may feel really awkward at first. But with time, you’ll start to feel more comfortable in the role, and be able to get more out of them. Likewise, it’s going to take some time to iron out the creases of your team management plan. You’ll need to keep track of what kind of feedback your team is responding to, and what they aren’t.

Above all, your role is to communicate with your team. A lot. Like Pierre Nanterme says, we’re moving to a world that needs “instant performance management” from team leaders—which involves a lot of communicating on your part.

Being a team manager can be really hard. You’re expected take on a lot of roles that might not feel really comfortable at first. But by putting these simple management tips in place, and practicing them over time, you’ll be a pro in no time.


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