Stop Overcomplicating It: The Simple Guidebook to Upping Your Management Game

Stop Overcomplicating It: The Simple Guidebook to Upping Your Management Game

Russ Laraway wades through all of the competing opinions, complex frameworks and advice out there on how to be a better manager, creating a simple, data-backed leadership toolkit.

Pick up Russ Laraway’s new book, titled “When They Win, You Win” and the first sentence is sure to grab your attention: “Managers are failing everywhere, and no one is helping.”

With that framing in mind, when we sat down with Laraway to find out more about the lessons inside his book, his next sentence was just as unexpected: “I think the world has conspired to confuse the average manager and I believe that we don’t need another person’s opinion about what it takes to be a great manager,” he says.

So if managers are systematically struggling, and we don’t need any more opinions swirling around about what managers should be doing — why pen a book? “Instead of just more opinions, we need a simpler leadership approach that measurably and predictably delivers more engaged employees and better business results,” says Laraway.

And that’s what Laraway set out to do — weaving together tons of existing management studies from top-notch sources like Gallup, his own primary research, as well as thoughtful stories from his own decades-long career.

You might recognize Laraway’s name from the digital pages of The Review and on our In Depth podcast airwaves. He previously shared advice on the crucial conversations managers must have to develop their people and the essentials of employee engagement.

But for those who aren’t familiar with Laraway, here are his management bona fides: As a former military leader, he oversaw 175 Marines as a Company Commander before pivoting into tech. He spent seven years at Google, during which he won the company’s Great Manager Award. He also had a four-year stint at Twitter before teaming up with Kim Scott of Radical Candor fame to found Candor, Inc., a software and content company to help companies make authentic, constructive feedback a cornerstone of their cultures. Next, he took on his first C-Suite role as the Chief People Officer at Qualtrics, before taking on his current role as CPO of Goodwater Capital.

From the Marines to software to VC, Laraway has spotted a pattern that frequently crops up and muddies the waters for managers everywhere. “People have become far too focused on all the things that should be different about being a manager: Whether you’re at a big company or a startup. If you're an engineering or a sales leader. If you’re in tech, food services, or manufacturing. We try to identify the things that are different and therefore should be different in our leadership approach. This is the exact wrong instinct,” he says.

There’s one common ingredient across every type of manager: You’re leading people. So the core of what makes for good management can’t be all that different, whether you’re leading a team of baristas or engineers.

In this exclusive interview, Laraway sketches out the lessons in his new book that apply to managers everywhere — from the “Big Three” management frameworks most strongly correlated with employee engagement, how to measure how well your managers are performing, and how to make sure you’re even picking the right leaders to begin with. He skips the fluff and instead leans on quantifiable research to chart a clearer path to management success. Let’s dive in.


There are plenty of frequently-touted theories for why managers misstep (like a lack of good training or being so over-booked they can’t focus on what the team needs, to name a few). But Laraway unpacks a few sneaky reasons managers are struggling that aren’t always cited.

1. Style over substance.

There’s no shortage of content out there about management and leadership — and that’s precisely the problem, says Laraway. “I call it the lunch line problem. There are so many different management frameworks out there, and you just pick and choose whatever resonates in the moment. There might be a new ‘flavor of the week’ model that a CEO gets all jazzed about, like situational leadership, and wants to share with their company. It’s immensely confusing for the modern manager,” he says.

As an added layer, there’s an increased focus on bringing an individual leadership style, unique to yourself or the company you work for. But this approach is missing the forest for the trees. “Nobody ever applies for a job called 'leader.’ The job is usually called ‘manager.’ We have to restore dignity to the office of the manager. I’ve found that folks are too focused on finding really complicated, cool leadership-y things for their unique environment, instead of just focusing on the stuff that works pretty much everywhere,” says Laraway.

We’ve allowed ourselves to fall victim to this idea of grandiosity — that leadership is better than management. We focus on the esoteric, complex ideas that make us a “leader” rather than the specific things managers must do well.

Along those same lines, Laraway sees that folks tend to overweight the value of charisma when it comes to sizing up their leadership chops. “I like to put it this way — the successful managers brush and floss, while the charisma folks are the teeth whiteners. The brush and flossers do the little things every day that lead to the employee being successful,” he says.

“The one thing every single one of us has in common at work is that we want to be successful. So whether or not a manager has charisma is irrelevant in that context. It’s the person who does the grinding work each day or week to make their team members successful. That’s who people ultimately want to work for,” says Laraway.

To me, the job of the manager is so freakin’ simple, consisting of only two things, that it actually gets me a little hot under the collar when we overcomplicate it: 1) Deliver an aligned result. 2) Enable the success of the people on your teams.

2. The system for choosing managers is broken.

Across the board — from mom-and-pop restaurants to global enterprise companies — Laraway sees a negative pattern crop up over and over again when it comes to elevating folks into the manager role. “We tend to select managers either based on their tenure or because they were the best individual contributor on the team,” he says. Both are particularly applicable for startups, where most folks tend to start out as ICs in the earliest days. From there, once more folks come on board, the founding engineer likely gets promoted to lead the engineering team. And as the team grows, the sharpest engineer IC ends up hiring folks underneath them, and so on.

This is a big mistake with trickle-down effects for years to come, says Laraway.

The activities that make you successful as a manager look nothing like the activities that make you successful as an individual contributor.

Instead of defaulting to the longest-tenured person in the room or the one with the most accolades, Laraway suggests getting really specific about the leadership behaviors that you expect from the folks who take on management duties. “Instead of this nonsense like judging people on whether or not you want to get a beer with them, which is totally susceptible to bias, you need to develop a rubric. That gives you a much better chance of finding people who abide by the management values that you’re looking for — whether that’s promoting an internal employee, or hiring someone externally,” says Laraway.

To get started with your own management hiring rubric, copy this template from the “When They Win, You Win” toolkit.

Consider this example: “Let’s say you have a group of salespeople and you need to promote one to manager. You may be concerned that if you don’t promote the top quota attainer that they’ll leave your company. It takes a lot of gumption to pick the worst quota attainer,” he says. “But maybe that lower-performing salesperson is a really strong communicator. Or the higher quota attainer has a higher inclination to act in self-interest. Being an exceptional IC is less important than we would imagine,” he says.

Think about the conductor of a symphony orchestra. They may not have been the best individual player — and that doesn’t matter. Their job isn’t to shine as a soloist, their job is to lead a group and make sure they’re all playing together.


If employee engagement is directly tied to business results, and managers are the single biggest factor in employee engagement, it became critical for Laraway to clearly articulate the specific behaviors that power up employee engagement levels on the team.

Through his own research studies (for the details here, you’ll want to pick up the book), he determined a list of three specific management behaviors most closely aligned with employee engagement.

  • Direction: Good managers ensure that every member of their team understands exactly what is expected and when it is expected.
  • Coaching: Good managers coach their people towards both short and long-term success, helping them understand what they should continue to do and how they can improve.
  • Career: Good managers invest in their people’s careers in a way that considers their long-term goals and aspirations beyond the four walls of the current company, and certainly beyond their next promotion.

We’ll dive deeper into each one below, including specific behaviors you can implement right away that make a difference.

Russ Laraway, author of "When They Win, You Win"

Set direction.

While “direction” might seem a bit fuzzy, Laraway brings it into clearer focus with four distinct pieces (his book dives much deeper here, but we’ll give you an abridged overview). “Direction-setting anchors the team to an aligned result through the combination of two long-term elements (purpose and vision), and two short-term elements (OKRs and ruthless prioritization),” he says. “Each element cascades to the next — purpose leads to vision which leads to OKRs, which leads to priorities.”

  • Purpose: “Purpose is often synonymous with mission. It’s the reason the company and the team exists — your purpose can last for decades,” says Laraway. For Twitter, as an example, the company purpose is: “To give everyone the power to create and share ideas and information instantly without barriers.” While you may not be architecting the company’s purpose from the CEO perch, Laraway recommends managers assemble their team with just one agenda item: Define your team’s core purpose. Prompt some thought starters with questions like: Who do we serve? Why do we matter? What do we produce?
  • Vision: “While purpose is why you exist, your vision is the mountain you’re jointly trying to climb. The vision is quantifiably measured whether or not you achieved it — even if it’s many years in the future,” says Laraway. For example, the current vision for SpaceX is: “Enable people to live on other planets.” To get started, Laraway suggests this exercise with your team: “It’s three years from now. The CEO is holding a party in our honor. What happened that caused them to throw this extremely expensive party?”
  • OKRs: OKRs are the quarterly or annual goals that get you closer to achieving your team vision. “The only time I am likely to get accused of being a micromanager is around goal-setting time, which is usually the two or three weeks preceding a new quarter. This is because once we have clarity on the goals, I am in a much better position to grant folks the autonomy they need to achieve them,” says Laraway. But even within this hyper-focused state, it’s critical to leave room for other voices. “When determining your team’s goals for the quarter, a big part of your job as manager is to gather their input. After all, it’s their team too. The simple practice of asking the team ‘What do you believe we should be achieving together?’ gives them a lot more skin in the game and a much greater feeling of ownership in the outcomes.”
  • Ruthless prioritization: “I believe priorities is one of the most misused words in tech. People often say their task list is their priorities — wrong. Prioritization is an exercise in subtraction, not an exercise in addition. If you have more than three priorities in a week, you don’t have any. You just have a task list,” he says. “I find folks often nod their heads that prioritization matters, but then go on chasing workstreams that just don’t matter. It’s about focusing on a very small number of things that matter to the business, being most effective at those things, and perhaps recapturing some work-life sanity.”
Overachievers abound, but they often confuse volume of work with impact. The manager can help provide that clarity and give those folks permission to do less. If the manager doesn’t do that, who will?

Start here: Add this phrase to your standup meetings.

Even well-meaning managers can often fall into one common trap. “There’s nearly always a gap that exists between how clear the manager thinks they are being with the team, and the clarity that is actually provided,” says Laraway.

You likely already have weekly team standup meetings on your calendar (and if yours is in desperate need of an overhaul, consider these tips). During these meetings, ask each team member to articulate their three priorities — and be really strict about sticking to three. “Don’t let this turn into an arms race where someone starts listing four, and another then does seven. This exercise isn’t about getting visibility into every single thing folks are doing. This is about doing the hard thinking about the most important thing folks need to get done today or this week,” says Laraway.

And for managers, add one particular phrase to your repertoire to continue to bang the drum of what matters most. “Ask the question: Which quarterly goal does that workstream support? If you keep finding that the work that you’re doing isn’t reflected in the quarterly goals, it’s time to rethink how you’re approaching those OKRs, or get them right the next time,” he says.

Provide coaching.

Up next on the list is coaching, which comes after direction for a very particular reason. “Coaching enables team members to achieve those desired results,” says Laraway. “It comes in two forms: coaching to improve what’s not working, and coaching to continue what is working.”

And while much ink has been spilled teaching folks to get better at delivering tough feedback, there hasn’t been nearly enough attention paid to helping folks explicitly understand what they have done well so they can do more of it. (As Molly Graham so aptly pointed out, we tend to pay much more attention to the lower performers when we should be paying attention to our high performers.) “Often, your manager will just walk up to you or ping you on Slack and say ‘good job’ before walking away,” says Laraway.

When managers get ready to give hard feedback, they do a lot of prep work. Maybe they write a script or even go through a practice session with a friend. But think about how little work goes into giving folks praise.

He borrows a phrase from Kim Scott: Be specific and sincere. “‘Specific’ is the most important word here. As managers, we’re not cheerleaders — we’re coaches. Saying, ‘Good job,’ isn’t good praise for good work, because it’s just not useful,” says Laraway. Here’s how he clarifies the difference. “When you say something like, ‘You know what I really loved about the way you held that customer presentation…’ and then offer specific things that you think went well — that’s good coaching. Articulate the specific things that lead to success, because then someone knows what behaviors they should repeat.”

Start here: Invite feedback from your team.

While providing feedback is a critical part of the managerial job description, asking for feedback from your directs is another key piece of the puzzle that often gets left behind. “The folks that we’re hiring for want to be heard. They want to have some skin in the game. If you have a manager who doesn’t go out of their way to make sure everybody’s heard, people become disengaged,” says Laraway.

The key here is soliciting feedback — and doing so in a very particular way. “You have to learn how to skillfully get people to tell you what they really think — most folks won’t feel comfortable just giving you their direct feedback unprompted. And just saying, ‘Can I have some feedback?’ is not going to cut it,” he says. Try these questions instead:

  • Is there anything different I could be doing that would help you be more successful?
  • What would you like to see more from me?
  • What would you like to see less of?
  • Something felt off in that team meeting — do you have any insight on what I could have done better?

And what happens next is equally important — you need to listen and resist the urge to get defensive. “You cannot penalize the person for speaking up, or you end their willingness to provide feedback in the future. Just listen without responding or interrupting, and then ultimately you have the discretion to act on that feedback or not.”

Consider their long-term career.

“Career is the most overlooked element, but it is critical to employee engagement. A manager must do more than help employees succeed in the job they are doing now; they must help them discover their long-term vision for their careers and show them what actions they can take right now that will allow them to make tangible progress toward it. In doing this, you show employees that your care for them extends beyond what they can do for you or the company,” says Laraway.

The analogy he tends to lean on most is the idea of a “gravity assist slingshot.” “If you’ve ever seen a space movie, there’s often a point in the film where the mission is going awry. The rocketship is low on fuel, but the gang has got to get into the farthest reaches of the galaxy. So they’ll do a gravity assist slingshot where they use a planet’s gravity to propel them out further and succeed on their mission,” he explains.

The most common trap Laraways sees well-meaning managers step into is forgetting to look into the far reaches of the galaxy. “Managers often think about the employee sitting across from them for just a small period of time — maybe you’re only working together for a couple of years. But that person is on a much longer career trajectory, both before you became their manager, and long after you're gone,” he says.

Remember — your job as a manager is to be the gravity assist that slingshots your employees into the next galaxy of their career.

Start here: Change up your career conversations.

Maybe you already have annual career conversations on the calendar with your direct reports. Most likely, those one-hour meetings are focused on the relatively short term: What do they need to do to get a promotion in the next year?

To widen the aperture, Laraway prescribes three specific types of conversations (to really dig in here, check out his more thorough explainer on The Review):

  • Start with the Past — Life Story: “In the first conversation, make an effort to understand the employee’s motivations and values, the things that drive them. You should focus on their major pivots and transitions, including athletics choices, hobby choices, study choices, and work choices. Why did they make those choices? What did those transitions teach them about what they love and hate about their work? This is the path that led this human being to this moment in time.”
  • Talk about the Future — Dreams: “Conversation two is where you ask questions designed to discover where this person wants to be at the pinnacle of their career. Some are skeptical that our younger workers know what they want to be when they grow up. Others worry that it’s too early in a career to home in on a single vision. Don’t use those worries as excuses; nothing is irrevocable at this stage.”
  • Plan for the Present — Career Action Plan. “With a firm understanding of the past and the future, now you can begin to build a relevant and thoughtful action plan, with clear timelines and explicit owners for each action. Expect little to happen if you don’t fill in the blanks of who will do what by when. We can see the path behind us, we can see the lighthouse in the distance, and now we just need to start swinging our machete through the vegetation so we can cut a path that connects the two. Once we understand the past and the future, we’ll know what we need to do right now.


With that framing in mind, founders and org leaders should do a gut-check — how well are your managers performing? You could go in a bunch of different directions here, from manager OKR performance of their teams and attrition rate, to employee advancement and promotions. But in the spirit of simplicity, Laraway leans on two surveys to get started — employee engagement surveys and manager effectiveness surveys.

It doesn’t have to be complicated — employee engagement surveys have stuck around for a reason.

“Engagement is strongly correlated with business results. Gallup found that companies in the top quartile of employee engagement have about 90+% better earnings per share than their competitive set. I can’t think of a more precious business result for a publicly-held company than earnings per share,” says Laraway. “But folks tend to get caught up in what engagement actually means. Let’s simplify it here — you can actually measure engagement with a very standard, composite scale,” says Laraway.

For starters, he recommends setting up a straightforward engagement survey if you don’t have one already, with employees answering each question on a five-point scale:

  • Overall, how satisfied or dissatisfied are you with [Employer] as a place to work?
  • How likely are you to recommend [Employer] as a place to work?
  • How willing are you to put in effort beyond what is expected?
  • How fulfilled are you by the work you do?
  • How much do you agree with the following statement: “I’m proud to work at [Employer]”?

With just these five questions, you can measure engagement company-wide, and compare across different teams and departments.

Want an easy way to get started? Copy this Employee Engagement Survey template directly from the “When They Win, You Win” toolkit.

Drill down deeper with manager effectiveness surveys

So, with the stakes set, that employee engagement is directly correlated with business results, the question then becomes — what moves the needle on employee engagement? “It’s the manager, more than any other factor — there’s not even a close second place,” says Laraway. As Gallup found, managers account for at least 70% of the variance in employee engagement scores across teams and departments. In other words, managers are holding the keys.

Everything else you’re doing to affect engagement is worth less than half of whatever you’re doing to make your managers great.

In addition to equipping managers with clear, comprehensive manager training, add manager effectiveness surveys to your regular rotation. “Once you understand the Big 3 leadership behaviors you want to see, you want to measure the frequency with which those behaviors of direction, coaching and career are being exhibited,” says Laraway. You can add additional questions to this list, but make sure you include these 12. These are also measured on a five-point scale, just like your employee engagement survey.

  • How helpful is your manager in helping you navigate company changes that impact you and your job?
  • How clear is your manager's communication of what is expected of you?
  • How helpful is the feedback provided by your manager in improving your performance?
  • How consistently does your manager provide you specific praise for good work?
  • How responsive is your manager to your ideas or concerns?
  • How supportive is your manager of your growth and development?
  • How frequently does your manager solicit feedback from you?
  • My manager cares about me as a human being.
  • How helpful is your manager in prioritizing your work, including helping you figure out what not to work on?
  • How collaborative was your manager with you when setting your individual OKRs?
  • How collaborative was your manager with you when developing the team's OKRs?
  • How comfortable do you feel going to your manager with a safety concern, no matter how small?

To get started with understanding how the managers at your company stack up with these key management behaviors, copy this Manager Effectiveness survey from the “When They Win, You Win” toolkit.


Every company, from early-stage startups to BigCos, wants to retain its top talent. And in that pursuit, execs tend to throw tons of darts at the board to see what sticks — from learning and development opportunities to unique company perks, and crafting a one-of-a-kind culture.

But according to Laraway’s research, there’s one single factor that most directly correlates to employee attrition: Whether or not folks believe their manager cares about them as human beings, not just worker bees. “It’s a fascinating insight — of all the fancy things companies try to do to address retention problems, the answer is often as simple as someone feeling like their manager cares about them,” says Laraway.

So for all the managers out there, whether you’re a first-timer or a seasoned leader, Laraway hopes his words of advice release some of the pressure to be perfect. “Very often, managers feel lost and alone. They’re expected to have all the answers and they’re afraid to ask for help. Worst of all is that combination of guilt and frustration that you don’t know how to make things any better,” says Laraway. “I want to set all managers free. You don't need to have every answer. You just need to know where to go find them.”