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Your Startup’s Management Training Probably Sucks — Here’s How to Make it Better

“Everyone quotes this Steve Jobs line: ‘Hire smart people and get out of their way.’ I’ve heard this my entire career, and I continue to hear leaders quote it all the time. It’s wrong for two reasons: First, Steve never said this — Ford’s Lee Iacocca did. Worse, though, is that it’s often cited when saying management doesn’t matter. But if you ask 100 people about their lived experience of being managed, 100 people would say that it mattered,” says Melissa Nightingale, co-founder of Raw Signal Group. “I never met Steve, but from everything we know about the Apple story, I don’t think he was one to stay out of people’s way.”

And yet, the ethos of that quote (and what it indicates about management) persists in founder circles. Particularly at early-stage companies, where you’re still wrestling with product/market fit and building up the company foundation, management often falls to the back burner, leaving folks to generally figure it all out for themselves.

However, many of the cracks that emerge as startups scale can be traced back to those missing managerial cornerstones. “Below 1,000 people, a lot of organizations run into problems that are very clearly those of an under-equipped management team: Alignment issues, siloing, conflicts between teams, three different departments shipping variations of the same thing without talking to each other — those all stem from management,” says Johnathan Nightingale, co-founder of Raw Signal Group.

One root cause? Manager training, which is largely ignored by startups as a BigCo bucket list item to be checked off later. “As an industry, we’re making progress on this front, with larger organizations bringing in formalized management training. But for scrappy companies, the overwhelming majority still have no training for people managers,” says Melissa.

Both Johnathan and Melissa Nightingale have felt these growing pains acutely in their own tech careers — and their experience probably sounds familiar to plenty of startup folks. “Johnathan and I met in the very early days of the web, working at Mozilla when it was sub-50 people, and growing really fast. We both grew with the organization as it passed 1,000 people. We got promoted into management to lead teams because we were really strong individual contributors, but we didn’t get any training on how to manage. We quickly found out that the expectations of being a great manager are wildly different than that of an individual contributor,” says Melissa.

There are a lot of people who have been given power in an organization, but no training on how to wield that power.

Many column inches have been devoted to tackling the thicket of challenges in front of a brand-new manager. But startups have been slow to catch up when it comes to implementing sound leadership training. “Power is weird. Being a peer and then becoming someone’s boss is weird. Giving feedback to a friend is much different than giving feedback to someone you can fire or promote. From outer space, we can see all these changes coming, so it’s wild that companies will let new managers walk headfirst off these cliffs,” says Johnathan. “But when folks come to management with a learners mindset — and are supported by the right systems and training — that’s where managerial magic happens.”

After leaving Mozilla, both Melissa and Johnathan went on to startups, including Wattpad (Melissa) and Hubba (Johnathan). But those early management stumbles stuck with them, and the married couple decided to team up and found Raw Signal Group, a management and leadership training organization. They also went on to pen a popular biweekly newsletter and two bestselling books: “How F*cked Up Is Your Management?: An Uncomfortable Conversation About Modern Leadership” and most recently “Unmanageable: Leadership Lessons from an Impossible Year,” something of a time capsule of the challenges managers faced in 2020.

“Startups have a healthy dose of skepticism about the established way of doing things and nowhere is that more prevalent than in management and leadership training — because it often comes from a very stodgy, dull place,” says Melissa.

When you hear “manager training,” you may think of snooze-worthy PowerPoint presentations and awkward role-play exercises. In this exclusive interview, Melissa and Johnathan Nightingale offer an alternative approach, honed from teaching thousands of leaders how to be better bosses. They talk through the common mistakes they see startups make when it comes to manager training, and offer super-tactical advice for companies looking to get it right and make leadership training a priority early on. Let’s dive in.

Johnathan and Melissa point to a few key phrases that they often hear from founders that indicate it’s time to start making manager training more of a priority. “For venture-backed startups, it’s always a flag when we hear early-stage founders saying: ‘We’ve doubled in size, but we haven’t doubled our output. It feels like we’re going slower,” says Melissa.

When you’re a really small startup, co-founder drama is the likely company-killer. But as your org gets larger, the thing that often tanks the company is waiting too long to bring on competent management.

When talking to founders for the first time, Melissa leans on a simple assessment question: “‘How big is your organization today, and what size are you planning to be by the end of the year?’ The planned growth trajectory tells you so much about what struggles are likely to crop up in the organization,” she says.

The Raw Signal crew also points to a few general milestones that most often cause founders to pick up the phone and ask for help with management training:

40-person org: “Stuff starts to get hard that used to be easy. The nostalgia sets in — we all used to fit in one room and talk to each other, and we don’t anymore. It’s gotten complicated.”

70-person org: “This is where silos start to creep up. You don’t necessarily know everyone at the company. We’ve seen these challenges happening even sooner during the pandemic because folks are working with people that they’ve never met in person.”

120-150 person org: “There’s a big cliff at this marker because the company is becoming a fractured culture. Nobody knows what anybody else is doing. At this point, we might not get a call from a founder, but from the HR department. There’s a cultural rift that can’t be fixed in an all-hands meeting.” 

350-person org: “At this stage, companies are much more bought in that they need to bring in some sort of leadership training. It’s about bringing in the right level of process — not tanking their ability to move quickly, which is what made the company successful in the first place.”

Founders — look for canaries in the coal mines.

As a startup grows, the founding team becomes one step (or a few steps) removed from the chaos of the day-to-day. The Raw Signal team advises folks to lean on both qualitative and quantitative data. “HR leads tend to have a clear idea of what’s going on in different parts of the organization, and where there’s friction. Sometimes it could be Finance leads. You’re looking for leaders who are working with a bunch of different parts of the organization at any given moment — they have the pulse on where things are smooth, and where they aren’t smooth,” says Melissa.

That said, repeat founders have a leg up here. “Serial entrepreneurs tend to come to management training much earlier. They often have stories from their last company, and are more acutely aware of the impact of training leaders and managers within the organization sooner,” says Melissa.

“When we first founded Raw Signal Group, there was very little training out there. I believed that any training was better than nothing. Orgs that had some training in place (no matter what it was) were better off than those that took a ‘throw them in the deep end’ approach to management,” says Melissa. “But over the past five years, we’ve seen a lot of programs that were actually worse than nothing, turning participants off of management completely because they’re so poorly run. If you aren’t thoughtful about how you build and execute these programs, you can end up making a giant mess of things.”

As an example, the Raw Signal folks had worked with a company with a deeply-technical workforce that had previously done some very corporate, dry management training. “It was a complete failure. Leaders were frustrated that most folks failed to even complete the mandatory training. It had gone so badly that the company declared a hiatus on the training while they regrouped,” says Melissa. “To combat this, when we rolled out new training, we made it entirely optional. Understanding that managers were uncertain about the value of training and giving them space to warm up to it made a massive shift in how the program was received. After our first cohort of opt-in manager trainees, the word of mouth buzz got other folks excited to attend.”

The good news? Folks want to get better, given the right tools. “The experience of being an untrained manager is so hard. It’s stressful to show up every day and not know how to answer the questions from your directs. Or to know you have feedback for your people, but don’t know how to frame it,” says Johnathan. “When you give those people actual skills, you don’t have to push them very hard to use them — it’s water in the desert. You’re able to give directs feedback in a way that’s not going to blow up your management relationship, but instead, they will receive the feedback and get better from it.”

People often think they don’t like management training. But what they’re really saying is “I don’t like shitty management training.” That’s different than saying “I don’t enjoy learning new skills that make me better at my job.”

The duo sketches out some of the other big mistakes they see from well-meaning startup folks when it comes to leadership training.

1. Trying to build training in-house.

While first principles thinking can give startups an edge, creating manager training from scratch is often not a worthwhile endeavor. “If you’re not planning to be the best in the world at some system, you don’t tend to build your own. It’s why startups use somebody else’s payment provider or someone else’s CRM,” says Johnathan. “But we meet small startups who decide to develop all of it in-house because management is very close to their own culture. Sooner or later they realize that there’s so much content to cover and they have to build out an entire learning and development team to create a custom program.”

Alternatively, many founders toss the ball over to the HR department. “Many founders think, surely this is an HR issue. So they ask HR to put together a presentation on building a feedback culture or doing 1:1s. But many of the people who are skeptical of manager training to begin with are skeptical of HR as a function,” says Melissa. “It’s very easy to say, ‘I’m an engineering leader or a sales leader. What HR has put together sounds great based on HR, but that person has never led engineering or sales.’ So they choose to ignore all of the things shared in the presentation because they don’t think it applies to them.”

2. Only training new managers. 

For orgs that have already implemented some degree of leadership training, the Raw Signal folks see plenty that roll out training just for new managers. “This leaves the entire mid-senior and exec layers under-equipped,” says Johnathan. He points to a few friction points:

No one wants to attend a remedial program. Even if senior folks are interested in some more training, they won’t join a program geared towards new managers.

New managers fresh off of training often bring in techniques and tools that are unfamiliar to their own bosses — and these suggestions are likely to get squashed with “that’s not how we do things here.”

With that in mind, manager training for all is key. “Mixed cohorts outperform in most startup environments because you get a range of seniority and experience, and it’s how you make the program culturally relevant to the org,” says Johnathan.

3. Siloing manager training by department. 

Similar to siloing leadership training just for new managers, Johnathan and Melissa see these programs stumble at the starting line when it’s designated for particular departments in the org. “A common mindset is that manager training is all about helping managers work better 1:1 with their reports. But effective management training is about the entire org,” she says.

For example, training sales and engineering leaders separately. “Guess what happens when those leaders try to work cross-functionally? They talk past each other and have wildly different expectations. If your org is already siloed, separate manager training makes it worse. If your org isn’t siloed yet but you train leaders by department, watch how quickly silos form,” says Melissa. “Training should reflect the realities within the org. If eng is never expected to collaborate with sales, ok. But in most startups, the overlap of departments is where things fall apart. Management training should bolster those relationships.”

4. Snacks are good for the kitchen. They’re less useful for leadership lessons. 

With jam-packed schedules at a fast-growing startup, folks are often looking for the “Minimum Viable Training” option — the smallest, snackable option with the least intrusion on leaders’ day-to-day. “We often hear: ‘Can we fit it in a lunch-and-learn? How small can we crunch down the nugget of information so it doesn’t interrupt the ‘real work’ we need our managers to do?’” says Johnathan.

The MVT approach misses on several fronts. “First, it signals to leaders that the org doesn’t value effective management. Second, it doesn’t provide enough room to dive into the why behind best practices. If you’re trying to implement a new behavior, I need to understand why it matters and how to tell if it’s working. Deeply technical teams understand that without the why, they won’t do their best work,” says Johnathan.

He sketches out an example: “There’s a lot of training out there that’s very prescriptive: You must do weekly 1:1s, they must be 30 minutes, and the manager must set the agenda. Or, you must do quarterly OKRs. But people don’t leave with an understanding about what’s behind those ‘musts,’” says Johnathan. To leave more space to dive into the why, the Raw Signal Group founders typically work with management teams across six weeks, meeting on a weekly basis.

5. CEOs want to join in. 

The Raw Signal co-founders have seen plenty of CEOs with good intentions join in on manager training — to the detriment of the program. “Founders often come from a place of, ‘Yes I’m the founder, but I’m part of the team too.’ We love the humble energy, but we’ve never seen a team where the CEO or founders joining didn’t change the dynamic in the room. Even the most approachable and accessible CEOs alter the vibe,” says Melissa. “If you want leaders to do the hard work and bring honest, vulnerable questions to the training sessions, you need to design for that upfront. That starts with being clear-eyed about how power exists within the organization.”

6. Horoscopes ≠ skills development. 

In the past decade, there’s a multitude of personality assessments that have cropped up — you’ve probably taken at least one of them, including DISC, Myers-Briggs, Strengths Finder, and Enneagrams. “Many folks say these tools have opened up new understandings of themselves, and we’re generally fans of any tool that helps leaders reckon with how they’re showing up at work and identify areas of strength and weakness in their own leadership,” says Johnathan.

The problem lies when these tools for internal self-discovery are turned outwards towards team dynamics. Here’s why: “When I use a tool to learn about myself, I jump to the parts that I feel are really unlocking something important about who I am. The pieces that don’t resonate I will ignore. But when I apply those same traits to someone else, I don’t have that deep knowledge to throw out the pieces that don’t quite fit. The tool makes others into shallow caricatures, instead of fully-realized people,” says Johnathan. “There are 16 Myers-Briggs types, four letters in DISC, and 9 Enneagram numbers. Trying to force-fit a team or a whole company into a framework like that oversimplifies things.”

If you’re a fan of any of these frameworks, there’s no need to throw them out entirely. “A training that employs any of these tools as a component of self-discovery is one thing. But training that’s anchored entirely on one of these tools is going to frustrate the participants when they leave the training session and try to put it into practice,” he says.

7. People hate role-playing — and it generally misses the mark. 

It’s possibly the most dreaded part of any leadership training — grab a partner and act out a scenario that demonstrates something you’ve just learned, like how to give difficult feedback to a direct report. In addition to being just plain awkward, the Raw Signal founders don’t find role-playing to be of much use. “Programs that use falsified constructs are difficult to apply when I’m back in my day-to-day context. It’s hard to deliver tough feedback to real humans. Delivering it to imaginary humans is designed to make it easier. But when I’m back in front of a real human, the things that were difficult are back again,” says Melissa.

Instead, the duo advises creating a space where managers feel safe talking about the actual struggles they’re having. “Whether it’s my own struggles or a peer’s, hearing them talk about it in real terms, and seeing how different tools or perspectives clarify things, is far more powerful and lasting,” she says.

Here are their tips for session facilitators looking to create the space for vulnerability:

Establish credibility: “We don’t come from 20-year careers as trainers. We come from 20-year careers doing exactly the kind of work we’re talking about. When we talk about techniques or models or perspectives, we bring in a lot of primary research to back it up, but we also ground it in real talk from our own careers,” says Johnathan.

Set up the space: “We’re big fans of Priya Parker’s book, ‘The Art of Gathering,’ including her model for setting rules of the space. That includes clarifying what confidentiality means in the session and asking everyone to commit to it. This creates a safe space where folks can show up differently than in their day-to-day,” says Melissa.

Go first: “The research is pretty clear that there’s reciprocity to vulnerability — they’ll only go as deep as we do, and they’ll go deeper when their colleagues do. We have plenty of our own struggles and mistakes to talk about, and we never ask them to talk about uncomfortable situations that we won’t bring up ourselves,” says Johnathan. “As an example, I often tell the story about the first time I had to fire someone and how I got so stressed out that I threw up in the parking lot afterward. I also made the mistake of talking about how hard I’d tried to make it work, purely to comfort myself instead of the person I was firing.”

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Melissa and Johnathan Nightingale, founders of Raw Signal Group

Whether you’re working with an outside firm or tasked with creating your own leadership training, the Raw Signal founders suggest that all training covers at least four particular modules. A few of these topics may not sound like things you’ve covered in past lackluster management training sessions, but they’re key to laying the foundation for fast-growing startups.

Goal setting: “As a company, how do you set goals? Whether it’s OKRs or one-page strategic plans, how do those goals flow from the senior levels down to the more junior levels? Whatever system you use, there needs to be training around how the business operates.”

Talent management: “This is the piece most people think of when it comes to manager training — the day-to-day people management. Stuff like 1:1s, giving hard feedback, holding career conversations. But something people tend to skip over during manager training is talking about firing and how to do it right, which should always be covered in leadership training.”

Org planning: “In fast-growing organizations, we ask leaders to be active participants in growing their teams — and that work takes a lot of time. Doubling and tripling in size is a massive time investment from leaders.”

Leadership & culture development: “We always end on a module that talks about investing in your own resilience and self-awareness as a leader. It’s about understanding how you show up, and how that bleeds into the wider company culture.”

Across each module, the goal is to ground folks in their past experience as a direct report — even if they’re many years and titles removed from that more junior part of the org. “As you get more senior in the organization, it can be really easy to lose touch with what it felt like to not have much power. Or what it felt like to have a boss who’s constantly changing their minds. Or to have a boss who was mostly unavailable,” says Melissa. “So when we work with leaders, the starting point is to talk through experiences from their own careers. That way, when we talk about the actual skills, they’re grounded in why it matters and why this is work worth doing well.”

Let’s take a deeper dive into each of the four pillars.

Module 1: Goal setting

We like to start each training session from a more philosophical place: Why are you here? What do we pay managers to do? To perhaps oversimplify it, the root of management is to make your team more effective. And the best way to make your team more effective is to be thoughtful and intentional about supporting their creativity and developing a high-trust environment,” says Melissa.

From there, the conversation flows towards how you organize a group of people centered around a set vision. “Regardless of whether they’ve got OKRs or OPSPs or Rocks, it’s not about prescribing a type of framework. It’s about how leaders view their role in taking that strategic vision and translating it into what actually happens when folks are typing on their keyboards,” she says.

Revisit that annual or quarterly plan.

While goal setting may not be frequently-cited in manager training, the Raw Signal folks believe it’s a critical anchor to the conversation. “It’s about building that predictive ability. Can you as a leader stare down what needs to get done in the next quarter and evaluate if you’re resourced appropriately? We want to avoid folks working evenings and weekends trying to make a goal happen that they knew in January was unlikely to be accomplished,” says Melissa.

That means pulling up those annual plans during manager training and digging in. “I remember once working with a group of leaders and we were talking about how if you have too many goals on your list, it’s hard to get them done and predict which ones might fall through the cracks. A manager put up his hand and said, ‘Well, I’ve got 16, and I inherited a lot of those — some carried over from last quarter, some my boss told me to add them to the list. So what now?’” says Johnathan. “To that, my follow-up question is: ‘If you could only hit two or three, which would they be?”

The Raw Signal founders point to a disconnect that often surfaces between the executive and the middle-management layer. “What’s funny is at that same organization we heard from executives who are pulling their hair out, wondering why the managers don’t push back when they think they’ve overcommitted. It’s about teaching people how to facilitate those conversations up and down the org chart,” says Johnathan.

You’ll notice an ongoing theme here — management training should also emphasize cross-functional work. “The interesting work in an organization happens at the intersection of more than one team,” says Melissa. “That sounds obvious, but in a lot of organizations, you get promoted because of your amazing expertise within your craft. But guess what? Your craft is really different than other people’s craft and you’ll approach problems differently.”

For Johnathan and Melissa, the unlock here relies on abundant communication — even if it feels like overkill. “We work hard with leaders to articulate: This is what the project is. This is what the timeline is. This is what resourcing looks like. The more you can anticipate what are going to be the collision points with other parts of the organization, the more you can smooth over those handoffs,” says Melissa.

The people who will screw you over in your organization typically don’t work in your department. It’s not because those people are assholes, but mostly because they don’t have the same frameworks in their head as you have in your head.

Module 2: Talent management

While there’s plenty of management advice out there — how to hold a 1:1, performance review frameworks, and handling the emotional ups and downs on your team — the Raw Signal founders find that a key piece is often missing from the puzzle. “It’s great to give people practical tools they can apply right away, but it’s often not accompanied with ways to know whether or not it’s working,” says Johnathan. “You may decide to hold 1:1s every two weeks — how do you know if that’s having a detrimental effect?”

The Raw Signal crew suggests one simple question bosses can ask themselves to gauge the effectiveness of your 1:1s: How often are you surprised? “This can be around projects underway, conflict with other teams, prioritization, timelines slipping, or a key member of the team getting a competing job offer,” says Melissa. “On the flip slide, how often are you, as a boss, surprising your people? Do your directs have a Strong Change Response when you communicate a roadmap shift that you thought was pretty straightforward? Did someone threaten to quit over a tooling change?” If you find yourself or your employees perpetually surprised, you may need to increase the cadence or the length of your 1:1 meetings.

They also connect it to one of the thorniest tasks on a manager’s plate — feedback. “People know they need to be giving regular feedback to the folks on their team, but it often doesn’t go well. There’s a bunch of habits people can fall into — they pre-generalize, they try to read other people’s minds, or they give feedback about motivations instead of behavior. Management training is about understanding what the feedback is trying to do and self-assessing whether the feedback you’re giving is useful or not,” says Johnathan.

DEI needs a seat at the table here.

Another frequent misstep Johnathan and Melissa point to is avoiding often uncomfortable DEI conversations in your management training. “Any management training that doesn’t have a rooting and understanding of inclusion in modern organizations is missing an important layer. Anytime you talk to leaders about power, but you don’t talk about how that manifests in the marginalization of certain groups, you’ve missed an opportunity to have an important conversation,” says Melissa.

That doesn’t mean you expect your management training team to build your DEI strategy — the Raw Signal founders note there are plenty of DEI experts who folks should lean on here. But leaving conversations about DEI for a completely separate time misses the mark. “It’s astonishing, frankly, that in 2022 there are so many management programs out there that don’t speak to DEI. How are we going to teach managers about feedback without acknowledging that some people get wildly different feedback than others? Or some folks get different career opportunities?” says Johnathan.

Face the facts about firing.

Another topic that might get a bit uncomfortable — but is a necessary inclusion in any management training worth its salt — is what to do with an underperforming employee. “We have a module on firing in our own training and are deeply skeptical of any management training program that doesn’t talk about what happens when things go sideways. Not because you’re trying to make management scary, but because your employees don’t forget that they’re able to be fired. I don’t think we should let managers forget that responsibility, either,” says Melissa.

The Raw Signal team’s own module covers a spectrum here. “There’s a lot of under-performance that’s recoverable. Especially first-time managers often find themselves in a spot where the situation has spiraled, and they’ve been pressured by their own boss just to get it done with. Meanwhile, the underperforming employee has probably gotten unclear expectations the whole way, they’ve probably had 1:1s delivered by someone who’s not comfortable talking about under-performance, and now finds themself on a performance improvement plan,” says Johnathan. “Even worse, there’s often no way they can possibly graduate from the PIP.”

In addition to diving deep into managing under-performers, the duo also wades into the murky waters of firing with their leaders. “It’s one of the sadder modules, but it’s also really important. How do you know when it’s time to fire someone? How do you work in partnership with your HR and Legal counterparts to ensure you’re doing everything by the book? We often expect leaders to be able to walk in a room and terminate somebody’s employment, but no one has ever prepared them to lead that conversation” says Melissa.

Module 3: Employee lifecycle and hiring

For startup managers out there, this sentiment probably sounds familiar. “One of the common concerns for bosses is that they don’t have time to get any work done. And when you dig into why they feel that way, often the thing that’s taking up a lot of time on their calendar is meeting with recruiters and candidates,” says Melissa. “If in your role recruiting is expected to be a large portion of the work that you do, then we need to train you on how to work with your recruiting counterpart so that it isn’t painful on either side.”

It starts with deeply understanding the ins and outs of your new job rec — from the level of seniority you need, the comparables in the market, and crafting a decent job description. The Raw Signal folks also make sure to dive into the company’s compensation system. “When someone comes in and says ‘Can I have a raise?’ we want folks to know the ins and outs of their company’s policy, rather than get a big stomach ache,” says Johnathan.

Module 4: Leadership and culture development

The final piece of the Raw Signal program traces back to the company values plastered somewhere on a startup’s website. “You’ve got a values poster on the wall in the office that’s got eight adverbs — what do they mean? And do you all think they mean the same thing? It’s not meant to be a trap, it’s meant to uncover if they’re real. If I start at your organization tomorrow, can I take these as a guidepost for how I should behave and what behaviors are going to get me recognized?” says Johnathan.

There’s another frequently-cited quote in Silicon Valley that the Raw Signal folks gently push back on. “There’s a story from Airbnb where an investor told them explicitly: ‘Don’t eff up the culture.’ It’s a great quote, and I completely agree that if you screw up the culture a company can quickly fail,” says Johnathan. “But as a manager, I need to know how to operationalize that culture and put it into practice every day, especially as my team gets bigger.”

The Raw Signal team is very intentional about putting the culture module last. “Culture always comes at the end of our programs because you need all the management skills and the shared accountability as a leadership team before you can really grapple with the culture,” he says. “It’s important to have the leadership conversation that asks: Are you building the culture we want?” 

Do the values that you put on the wall actually reflect your real values, or are there different behaviors that will get folks promoted that you’re not willing to admit?

“One of the most disorienting things about stepping into management for the first time is that no matter how much you want it to be the same as IC life, it isn’t. Not the work you’re expected to do, or the problems you’re solving, or even how your calendar looks,” says Melissa. “While many folks know intellectually that management is different than individual contribution, most first-time managers are unprepared for how much changes so quickly.” 

In terms of easing the transition, the Raw Signal folks hope to tweak the initial message. “I’d love if every time we promoted someone to management, we said, ‘Congratulations, we’re excited about this next step. But I want to be crystal clear — this is a different role than what you were doing before. The things that made you successful in your past role are still relevant, but the things that will make you successful in this new role are different. They’re learnable, but it’s going to take some work,’” says Melissa.

Cover image by Getty Images / Maryna Terletska.

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