This article is a lightly-edited summary of the key takeaways from Molly Graham’s appearance on our new podcast, “In Depth.” If you haven’t listened to our new show yet, be sure to check it out here.
If you’re a long-time Review reader, you’ll probably recognize Molly Graham’s name. We’ve interviewed her four times — which very well may be a record — simply because the advice she has to share is always top-notch, expertly threading the needle of refreshingly simple yet still highly tactical.
That’s likely due to the fact that she has an incredible stable of startup experiences to draw from, the kind of stories that are unbelievably helpful for founders and startup leaders to hear. Graham got her start at Google, and followed some colleagues over to Facebook in the early days, where she helped kickstart the HR department (working on early performance management, compensation, and employee engagement systems), and also pitched in to tackle Facebook’s phone and mobile strategy. She then joined her Facebook colleague Bret Taylor’s new startup, Quip, to figure out the business side of the SaaS product, which sold to Salesforce in 2016. After helping to spin up the Chan-Zuckerberg Initiative, Graham consulted for a number of startups, including Lambda School, where she recently signed on full-time as the COO.
Here on the digital pages of The Review, Graham has previously shared candid advice firmly rooted in the many paths she’s tread over the course of her career, touching on everything from managing your emotions and the struggle of giving away your Legos, to codifying company culture and setting up your first comp system. The arc of her career in startups may not follow a straight line, but there’s a common thread to pull on. As Graham puts it, it’s her love for the “messiness of scaling” and figuring out what it takes a startup to go not from zero to one, but from one to two.
Today’s conversation is focused on what that incredibly challenging phase looks like from the manager’s perspective. Effective management isn’t a topic we’ve covered extensively with Graham yet, but it’s a subject she has strong opinions on and a vast well of experience to dip into. She’s seen time and time again how so many startup mistakes come down to oft-neglected general management issues.
In this exclusive interview, Graham shares her six rules for how to be a good manager. Some come seemingly out of left field, others are nuanced takes on common pearls of wisdom — but true to what we’ve come to expect whenever we sit down with Graham, all are useful rules of thumb for any startup leader or new manager to lean on. From the unassuming traps that even great managers can fall into, to why the best leaders spend more time with the highest — not the lowest — performers, Graham shares tons of practical tactics for taking your management game to the next level (along with references to robots and wilderness medicine).
We kicked off the conversation with a simple question: What is the job of a manager, and how do you know if you're doing a poor, good or epic job in that role? In her answer, Graham points us back to the fundamentals. “One of the big mistakes I see people make is conflating management and leadership. I strongly believe you can be a leader without being a manager,” she says.
Here’s how Graham articulates the difference: “Management isn’t telling people what to do. It isn’t setting a vision and aligning the work around it. That’s leadership. To me, the best leaders are able to not just say, ‘Here's where we need to go,’ but are also capable of bringing people along, inspiring them, and making the ‘why’ behind that goal clear,” she says. “True management is the act of making the people around you better. Management is about investing in people, figuring out who they are, what they're good at, what motivates them, and then aligning the work a company has to do with their role and their growth areas.”
If those seem to you like disparate skill sets, you’re not alone.
Sometimes you'll find management and leadership in the same person, but it's important to recognize that they often don't come together in the same package.
“Let's say you're working with a CEO who has extraordinary leadership skills, but doesn’t get joy from management or isn’t particularly experienced at it. You can often pair them with someone who’s a really great manager, the kind of person who’s great at laying out the work that needs to be done and organizing people around that work,” says Graham. “The truth is that there’s a bunch of different versions of high-performing teams and there's no specific recipe to follow.”
Graham goes deeper into why she feels it’s worth splitting hairs here: “Management is one of the hardest jobs in the world. Only people who have certain characteristics and certain ‘loves’ should be managers,” she says. “When I ask you, ‘What do you love doing?’ a great answer is ‘I love investing in people and I love making them better, into the best versions of themselves.’ If that really brings you joy, great — being a manager is one of the most powerful and high-leverage jobs inside of organizations. But if the answer is no, then I’d strongly encourage you to not be a manager.”
The job of a manager is to bring out the best in people. And that’s not something that many get joy out of.
Beyond the fundamental requirement that the job (to borrow an oft-repeated phrase) sparks joy, how can you tell if you excel at it? “The easiest way to see if you're a good manager is by running through these questions,” says Graham. “Are the people around you growing? Are they taking on more in scope? Are you seeing them change in terms of things they weren’t good at six months ago? Are you pushing your highest performers and watching them explode? Are you helping your lower performers figure out what's not working?”
This is one Graham brings up quite frequently. “Particularly with new managers, but also when it comes to micromanaging,” she says. Here’s why she finds it’s so important to reinforce this rule: “Generally speaking, high-performing teams are not made up of robots. They're made up of humans who are able to independently meet a goal. It's just a huge amount of wasted energy to try to create robots out of humans.”
Intelligent machine analogies aside, here’s how Graham often sees this dynamic play out in organizations: “You often see people trying to direct their team in terms of exactly how they would have done it. I see so many managers getting really bogged down in the literal process that someone is going through in order to achieve a goal. But at the end of the day, there’s only one thing that matters: Did they achieve the goal?”
Some of the best management relationships are the ones with the person who goes about it in a totally different way than you would’ve, but they still get there in the end.
“To get out of that mindset, I push people to focus on, ‘What is this person responsible for?’ not, ‘How are they doing it?’ As a manager, you can give feedback on the ‘how,’ particularly if it’s potentially destructive to the people around them, problematic in terms of draining too many resources, or when the folks you’re managing are more junior. But goals and expectations have to be set around the what,” says Graham.
This rubric can also serve as a yardstick for performance. “It can be a part of how you define seniority — how independently can this person achieve a bigger and bigger sized goal?” she says.
The best managers set expectations at the “what” level, not the “how” level.
“My first job out of college was leading wilderness trips in places like Patagonia and Alaska for a school called NOLS. Taking 16 strangers out into the woods and making them get along for 75 days was the best management training I’ve ever been a part of,” says Graham.
“And as part of that prep work to be an instructor, you had to take an 11-day wilderness first responder course, which covers what you'd need to know to take care of illness, including everything from heart attacks and broken legs, to sustaining someone when you're more than an hour away from a hospital, or knowing when to call a helicopter. They teach you a series of systems for when you come upon an accident and you're trying to evaluate what happened,” she says.
The first rule is to assess the scene. “Let’s say you're hiking along and you see a person lying down in the middle of the trail. You have no idea what happened. You need to first look around to see if there’s something dangerous to you, because if there is, you should actually not engage. It sounds crazy to say you’re not going to go help them, because the person may be dying, but the grizzly bear or whatever might still be there. And the point is you can’t help anyone if you also become a patient. So often one of the very basic things you can do is to turn around and leave to go get help.”
So where does the management lesson come in? “I've used that principle as a metaphor for management in the sense that it’s almost impossible to help anyone as a manager if you're drained and burnt out. As managers, we often think we come second, that we have to make sure the team is okay first,” says Graham. “And so we postpone our vacation or we work longer hours because we ‘have to be there for the team.’ But in doing so, you only end up draining your own energy, hurting your well-being and becoming a mess, not realizing that you're doing a disservice to your team members by making yourself into a patient. You need to be your best self for them,” says Graham.
As a manager, one of the hardest management skills is learning to take care of yourself first. It can feel selfish, especially if you're a giving person. But trust me when I say that unless you are your best self, there's no way you can make other people into their best selves.
For Graham, this rule can, in her words, “really change how you think about your team and also about your time.” To start, she often tells managers to assess their calendars, not purely for time management purposes.
“You should be spending the majority of your time with the people who are moving the needle — the folks who are your highest performers and have the potential to change the company,” she says. “It's really easy to think, ‘That person is so strong, they just take care of themselves. I'll go focus on the rest of my team.’ But I firmly believe that the majority of my time and coaching energy should actually go into people who are high-performing. They are the rocket ships that could end up running parts of the company someday.”
As managers, we often forget that we should be spending most of our time with the highest performers on our team.
“To me, as a manager you’re looking to bring out the maximal optimized version of each person. So when you have someone who’s doing really well, the question should be, ‘How can they do even better? How can you make their growth explode?’”
From a coaching perspective, that involves a lot of debriefing and reflecting, Graham says. Here are the two tools she leans on most:
“More tactically, I do a look back, look forward every month or two, or at the end of a project — whatever milestone that makes the most sense for that person's role. I ask them to look back on a project that they just finished and run through these questions:
What did you like about that? What felt good?
What did you hate about it? What didn’t feel good?
What's the most important thing you learned?
Do you want to do more of that type of work, or less?
What do you want to do differently next time?
What’s the next challenge?
What's the next big step or career goal you want to reach for?
What type of work do you want to take on, whether it’s a current project in the company or something that might potentially show up in the future?
“A lot of these questions are from a strengths-based philosophy of management, the idea being that if you can figure out the alignment between what people love doing and what they're good at, you can find the best version of them,” says Graham.
In essence, it’s about carving out the time to help an individual reflect on their learning, unpack what didn’t work so that they know what to change next time, and then look toward the next challenge on the horizon.
For Graham, this comes back to how managers can get more deliberate about teeing up the next trajectory-altering steps. “When I look back on my time working on mobile strategy at Facebook, figuring out the sales motion at Quip and learning about philanthropy at CZI, all of those challenges were huge stretches for me. I was lucky that people were willing to take bets on me. But these opportunities came my way because somebody saw me do something well previously and was able to translate that into how I might be good at this other thing,” she says. “As a manager, one of the best things you can do is to take your high-performers and make bets on them, stretching them and seeing what they're made of. Sometimes people are capable of 10X of what you have them working on today. You just have to help them get there.”
You need to constantly give your high performers stretch goals and big challenges where they might fail. There's no better way for them to rapidly show you what they're capable of.
Outside of these milestone-based look back, look forward settings, Graham has found that the more formal performance review offers up another opportunity for managers to go the extra mile for their highest performers.
“When I was at Facebook, Lori Goler wrote some of the best, most thorough performance reviews that I've ever had in my whole life. They were like three to four pages long, so she went above and beyond. There were a series of ratings at Facebook, and typically as a manager, you give just one overall rating for the person's performance that cycle, but Lori broke down my performance across a series of sections and then rated each section and used that to aggregate up the total rating,” says Graham.
“I think a lot of times when we talk about performance management cycles as HR people, we don’t want them to be too important because we want you to have these conversations all year long. But Lori showed me that while I always knew where I stood with her, the review was a powerful summary moment to both reflect on the last half and how things had gone, but also to push me on what she wanted to see next,” says Graham.
“In practice, this can be as simple as saying, ‘You've done great at this. And to take that to the next level, I would have to see XYZ,’ just as we do with lower performers when you outline what you need to see in order for them to meet expectations.”
Of course, not everyone you manage will fall into that upper echelon. In Graham’s experience, performance issues often come down to roles and clear expectations. “When I was managing a team I didn’t have tons of expertise in, like marketing or sales, I first started with: Do people's roles make sense? Do they know how they fit in? How they align to the business? Then the second piece is, do they know what's expected of them? Do they know what success looks like? 80% of the time when I go into a team that's struggling, the answers to those questions is no.”
If there’s a new role that’s been poorly defined, which is par for the course in the startup world, providing clarification is the first step. “Once you define it, you’ll usually find that someone who’s in that role isn’t actually a fit for what the business needs,” she says.
Below, Graham gets more tactical on how to better calibrate expectations.
Graham draws on an example from her time at Quip to illustrate this rule in action. “Early on at Quip, I met with a ton of sales leaders and early folks at SaaS companies like Optimizely and Atlassian, and asked them, ‘Who closed your first customers? How did you get your first 10? 10 to 50? 50 to 100?’ Almost invariably the first 10 often are closed by the CEO. The next 40 are closed by someone who doesn’t have the pedigreed sales background from an expected company like Salesforce,” she says. “I remember talking to one company where their first salesperson — of what is now a multi-hundred million dollar business — was a mattress salesperson who was friends with the founder. And he just closed a ton of deals and helped them figure out what their primary motion was, and then they hired someone to take that and scale it.”
This was the exact kind of murky, ambiguous beginnings that the Quip team found themselves in. “We were trying to understand what we were selling and who we needed to be selling it to. And when you're in that phase, it's really challenging to find the people who are truly exceptional at ‘figure it out’ mode, versus the people who need structure and clarity, and particularly in the world of sales, clear incentives and a clear plan,” she says. “And it turned out that we had hired people who ultimately needed more structure than I was able to give them.”
That realization prompted some tough, expectation-setting conversations. “I had to say, ‘I'm not going to be able to provide you with clarity. I actually need people who bring their own clarity and structure. And that’s because I don't have a lot of the answers right now. You seem like someone who actually wants a playbook, and I'm not going to be able to give it to you because that's just not where we are as a business. And I don't want you to spend two years inside of an organization where you're constantly feeling unsuccessful.’”
To be a better manager, you have to be really realistic about what you can control and what you can offer — and what you can't.
“I say this to a lot of managers inside of scaling organizations, because so much stuff is out of your control. You can't control the fact that it's chaotic. There's a lot of ambiguity. So you actually need to be blunt with people, both when you're hiring them and also when you're talking to them about performance. Sometimes they need things that you can't give them, no matter how hard you try.”
Here’s how Graham right-sized expectations in the sales scenario: “We implemented this sales compensation plan that Jason Lemkin shared. It’s all about alignment between the incentives of the company and the incentives of the salesperson. Essentially, you only make bonus money as a salesperson once you pay for yourself. So say you cost the company $100,000. Dividing that by four, you have to make $25,000 a quarter before you can get paid more. This isn’t a typical sales comp plan, but this approach exactly matched the phase we were in because we needed salespeople who were company-aligned,” she says.
“The expectation was clearly set that they need to be focused on making Quip successful first, with the upside coming after they’d taken on the work of figuring out what it takes to sell the product. We weren’t handing them something that was repeatable yet,” she says. “Some were able to crush that sales plan, and pay for themselves (and more) pretty quickly. Others struggled and were frustrated. But it was clarifying — both for myself and for the team members — that we needed people who were going to come in and make a playbook.”
Here’s how Graham approaches it on an individual level: “Most people can be exceptional and perform way better than they are today, under the right set of circumstances. And so the question for managers is whether those circumstances can exist in the role that that person is currently in, elsewhere in the company, or if it’s just not a fit at all,” she says. “When assessing a low performer, the most important set of exercises to run through are: What is this person's job? What is expected of them? Do they know that? And then once they do, do they have the desire and the energy to fix it? Then you can go to them and clearly explain, ‘Here’s what's expected of you. Here's what you're delivering. And here's the gap,’” she says.
“Not going through that exercise does a disservice to them. A lot of times when people are struggling it’s not because they're bad at stuff, but because they don't know what's expected of them. Give them the chance to see the gap and say, ‘I know I can do it,’ or ‘This really isn’t for me actually.’”
Often a low performer isn’t someone who is inherently low performing. It is someone who has the wrong set of circumstances around them — they’re in the wrong job or in the wrong organization.
“What I see most often is that many people have never gotten really good feedback. They haven't been pushed. Nobody's held up a mirror to say, ‘This is how you're coming off to the people around you. And here’s what's getting in the way of you being more effective, getting XYZ title, or reaching that goal you have,’” says Graham. “When you do deliver that kind of feedback, folks are often like, ‘Whoa, no one's ever said that to me before, or it was phrased completely differently.’”
Dan Rose was a huge influence for Graham in this area during her time at Facebook. “It’s relatively famous if you’ve worked for Dan before, but he shared this story recently on Twitter about the very blunt feedback Sheryl Sandberg gave him early on in his career and how it totally changed his life. He taught a lot by example, and would tell stories like this from his own experiences all the time. I felt like he was constantly pushing me and figuring out what I needed to do to be more effective. It’s invaluable to have someone say, ‘Hey, you really messed that up,’ or, ‘You need to step up over here.’”
People can grow and change at any point in their career. But I believe most people haven’t been given the chance to do so because they haven't gotten honest feedback. No one's held up a mirror to them about their work, how they impact others, and the things standing in the way.
“As a good manager, the first step is identifying that something's not working. The second step is having the conversation and saying, ‘Here's what I'm seeing. You're not meeting deadlines. You're constantly turning in work that's at about 80% of what I’d expect. And I want to talk about why that is,’” says Graham.
“Usually when you take the direct path and have those conversations with people, what you find on the other side is that they're struggling, they're confused and they don't know why things aren't working — but they also feel like something's not right,” she says. “And once you do this a couple times, you realize that people want to know where they stand. That’s why one of the things I always say is ‘Direct is actually kind.’ You may think it sounds horrible to say that something’s not working, but a lot of times, they're like, ‘Oh, thank God you said that. I also feel that way and you’re making space for me to actually say it.’”
Humans don't like having hard conversations. We build them up in our heads, and then we try to couch them in a lot of useless language that makes it hard for everybody to understand what's going on. One of the biggest management skills to work on is being direct with people.
Graham’s advice is to start on these communication skills as early as possible. “Have a foundational check-in conversation about how things are going with new hires. If you can talk about the five things that are going amazing, and the three things aren't working, it makes it so much easier three months later to say, ‘Here’s a bunch more stuff that's not working.’ If you start that habit early, it gets a lot easier to have direct conversations with people. But if you wait until something's really not working, then you end up surprising your direct reports and having worse conversations that are much more stressful.”
Tactically, here’s how she puts that into practice: “I always write down the number one message that a person needs to hear and understand. Then I try to make sure I say it a couple times in the conversation. The following week, I’ll actually have that person repeat it back to me to make sure we’re on the same page. ‘What did you hear last week? What’s your articulation of what’s going on?’” says Graham.
If you can hear back the same messages that you were trying to send, then you know you’re on the same page. That’s when you can start to focus on what you’re both going to do about it.
All that said, sometimes expectation-setting and delivering tough feedback still won’t close the performance gap. “I'm a fan of giving people multiple chances, but I'm also a fan of setting people free,” Graham continues. “When you actually look at how you spend your time as a manager, often you’ll find that you're spending the most time with your direct reports who are struggling. You're trying to help them not struggle, which is totally a worthwhile effort. But you have to be really self-aware here, because the fact is that sometimes people take up too much time,” she says.
“Spending huge amounts of your time trying to make someone else successful isn't always going to be sustainable, for you or the company. Sometimes it indicates you should think about having a conversation about whether this is the right fit for them.”
This, of course, is an area where it’s tough to get too prescriptive. “I wouldn't put a percentage on it because that can be dangerous. Saying something like, ‘We should be managing out 5% of people,’ can be a real drain on the organization and create a sort of a witch hunt,” says Graham.
But she’s not about to leave managers without a foothold to reach for. “I recommend looking at this: How many people have you hired in the last year? A lot of times, you'll see companies that are doubling, going from 50 to 100, for example. And then you ask, how many people have left the organization? In larger organizations, you can aim for 5% or 10% non-regrettable attrition, but that’s harder in a 20-person organization. But if it’s zero, then just look at that math. You’re assuming that you’re perfect at hiring, that you have a 100% success rate — which I've never seen before,” she says.
“So it’s more about actively asking these questions around if people fit. Most founders and management teams let people stay around a little bit too long — when it's clearly not working for them or for the organization. It’s particularly scary for first-time managers inside of smaller organizations, because you spend a lot of time assuming that it's your fault, and you think the person's going to be angry at you. But if you want an efficient, faster ship, you have to get good at having hard conversations and managing people out of the organization.”
I don't have a perfect set of numbers to go by here, but I will say that one of the best things to get good at when you’re a growing organization is recognizing who's not working out, and creating a process to help them find their way out. If you aren’t good at that early on, you won’t get good at it over time.
Cover image credit: Getty Images / David Malan