What I wish I’d known before I took the job: Insights and advice from top technology company leaders

It’s a sentiment many leaders have thought to themselves at some point on their career journey. Whether referring to the nuances of company culture, the unspoken stakeholder expectations, or the day-to-day demands that never made it into the job description, hindsight can be unexpectedly revealing.

“Many people land in situations that aren’t what they thought they’d be,” notes David Peck, global head of Heidrick & Struggles’ Coaching Practice. New leaders often share their surprise at discovering that the organization and team they’ve joined differed in meaningful ways from what they expected—and they frequently express a desire to have had more clarity from the outset.

Yet these lessons are rarely shared. Often, leaders eventually adjust to their new environment or move on to another opportunity, leaving these valuable insights behind, unspoken and unexplored.

To explore this idea further and to help current and future leaders navigate transitions more effectively, we spoke with executives about what they wish they’d known before stepping into their roles. Their reflections are candid and insightful. They emphasize the importance of knowing oneself, conducting meaningful due diligence on potential employers, identifying allies early, and being prepared for the nuanced dynamics that come with the first days in a new role. Their advice also offers important takeaways for hiring managers and teams engaging with prospective candidates

The encouraging news is that, while wishing you’d known more “can happen to anyone, the degree to which it happens depends on the prep you put in up front and the perspective you maintain,” says Ryan Barretto, CEO of Sprout Social. Success in a new role begins well before the first day.

Our conversations revealed three key questions that all leaders can ask themselves to better prepare for any new opportunity, each aligned with a distinct phase of the transition: What should I do before beginning my search or engaging in interviews? What kind of due diligence is essential when evaluating a new opportunity? Now that I’ve stepped into the role, what should I prioritize to ensure early success?

What should I do before beginning my search or engaging in interviews? 

You’re between roles or considering a new opportunity. Now what? It is a straightforward question, but even experienced leaders can find it difficult to answer with confidence.

Leaders we spoke with, and our own observations, underscore the importance of using the transition period intentionally. Rather than rushing into the next opportunity, take time to reflect deeply on your experiences to date: the skills you’ve developed, the capabilities you have built, the gaps you want to address, and what truly motivates you going forward.

This “self-diligence” is crucial because it allows you to clarify your personal and professional goals, define what success looks like in your next role, and ensure you’re pursuing opportunities aligned with both your aspirations and strengths. As tempting as it may be to move quickly, investing in this self-assessment can be one of the most strategic moves you make.

Using a formal or informal framework can help, as Heidrick & Struggles’ Peck notes: “Get super clear about the type of organization, stage of growth, and challenges you’d like to take on. What’s most important to you in the role? What are your three to four must-haves—compensation, geography, culture, career alignment, work–life integration? What are the ‘happy problems’ you like to solve most, such as building or fixing? That’s your Venn diagram. Know the exemplar companies you’d join tomorrow, and don’t cast too wide a net.” 

“I knew I’d need support on lots of things stepping into the CEO role for the first time: P&L, partnering with the CFO, unit economics,” says Sprout Social’s Barretto. “So, I did research and shared them openly in interviews.” 

Jennifer Morgan, CEO at UKG, emphasizes the value of taking intentional time to prepare: “When I moved into private equity, it was a big shift: a different industry and business model. But I’d taken eight months off prior to reflect on what I’d done, what I was good at, and what I enjoyed so that in my conversations with my future employer I could align what I wanted and was good at with that opportunity, to help them do what they wanted to do in the market. I was honest with myself about my preferences and strengths, without letting my ego get in the way.”

She advises other leaders to look at the big picture and “do some soul searching. Make yourself vulnerable. Talk to trusted people who’ve seen you through different lenses to understand what you’re good at and where you’d fit best.”

And it can be helpful to look to mentors, coaches, and even organizational psychologists. For example, Zendesk CEO Tom Eggemeier has worked with an organizational psychologist for years: “She sees things about me before I do.” 

What kind of due diligence is essential when evaluating a new opportunity?

“It all starts with due diligence,” says Andy Kofoid, president of global field operations at Databricks.

Due diligence starts with knowing yourself—but it shouldn’t stop there. What we heard from leaders is that while self-awareness is essential, its value is closely matched by the importance of understanding your potential future stakeholders. Knowing who they are, what they value, how they operate, and what they expect can make all the difference in determining whether a role—and the environment around it—is truly the right fit.

Go beyond the web

If you are considering a role at a certain company, that company’s website and online feedback platforms can offer useful insights into the organization’s structure, values, and reputation. Regarding online feedback platforms specifically, however, Erica Schultz, president of field operations at Confluent, offered a caution: “Take [some of what you read] with a grain of salt because the content is often negative. Go beyond that. Call the call center, talk to customers to put yourself in their shoes, talk to other top executives—your would-be peers—and the board.”

That sentiment was echoed by others. On the numbers side, it is essential to understand key performance metrics, such as revenue, growth rate, customer conversion, and other relevant indicators. If possible, ask the prospective employer to confidentially share data through a secure platform or data room to give you a clear picture of the business. If a private equity firm is involved, it can also serve as a valuable source for key financials and strategic insights.

Talk to a variety of people

Understanding the people is just as critical as understanding the business. Engaging with key executives, especially those you’ll be working closely with, is essential. Among them, the CEO is often the most important person to understand, particularly if you’ll be reporting directly to them or partnering closely.

You’ll likely spend a significant amount of time with stakeholders throughout the interview process, so it’s important not only to observe how they communicate and collaborate but also to stay alert for potential red flags or misalignments. In addition to assessing fit, bring the same focus and preparedness you would to any important conversation—this is as much about interviewing them as it is about them interviewing you. “Before I joined, I spent a lot of time with Justyn [Howard, former CEO of Sprout Social],” Sprout Social’s Barretto says. “Meetings, whiteboarding, lunch, dinner, texts, calls. You have to know who the person is professionally and personally—how their brain works and how their values align with yours, or don’t.”

Confluent’s Schultz had a similar experience: “I got to know the founder/CEO before joining and understood what made him tick. I saw firsthand his commitment to becoming a great company and leader.”

And it can also help to talk to former employees. “Try to find out what may not have worked out,” Databricks’ Kofoid says. “Get their point of view on what happened and why.”

“Look for back-channel references,” says Zendesk’s Eggemeier. “These are important to use in both directions—for you to understand the company and for them to understand you. I encourage anyone I’m interviewing to seek references in their network, beyond the ones I provide.”

UKG’s Morgan was on the company’s board before joining the business as a leader. “I had a view of the company through my own outside eyes, even more than those who’d been there a long time,” she says. “The executive chair [the former CEO of UKG] brought context and a learner’s mindset as a great guide when I was talking to them about joining.” 

Barretto echoed the point: “You need evidence this [relationship with the former CEO] will be a tight, trusting relationship.” 

Similarly, customers can be a key source of information. “Ask multiple customers probing questions: How is the company showing up in the market? Have they stumbled in serving you? How did the account team handle it?” says Barretto. “I had an engineer take me through the product demo as if I were a prospective customer.”

The board represents another vital group. “Try to talk to all board members to understand their thesis and the investors’ thesis,” Barretto says. “Go deep to understand how the product is differentiated and what the go-to-market strategy is.” 

Take a broad approach. “Never rely on just one person,” Kofoid warns. “Triangulate by talking to as many people as possible about what the product is like in real life, who’s the competition, and other areas.”

Collaborate to assess fit

While structure diligence is important, nothing replaces the value of working with the leadership team in some capacity. Whenever possible, explore opportunities to engage on a real business issue, whether through a short-term project, a strategic workshop, or a working session. 

This kind of collaboration offers a clear view into how decisions are made, how the team operates, and whether your working styles and values align. It also creates space for candid conversations and the opportunity to ask direct, thoughtful questions that go beyond surface-level impressions.  

This opportunity could also come through joining a leadership offsite, as Eggemeier has Zendesk candidates do. “The dynamic on the executive team can make or break both company performance and personal experience,” Confluent’s Schultz says. “Try to really get a sense for how they make decisions and interact. Ask questions like, ‘How do people bring a dissenting view?’ and ‘How does the team work through these?’” 

UKG’s Morgan agrees: “You have to feel it, see it, live it by meeting the people at the company and seeing what the company does well and doesn’t. For your part, overshare about who you are and how you operate so they can understand the full picture, too.” Heidrick & Struggles’ Peck advises candidates to “spend time working on how you’re going to work together—the how in service of the what.”

Avoid “happy ears”

No matter which sources you consult, it is important to listen with a critical ear and resist the temptation to hear only what you hope to hear. “Go in with a list of questions and take copious notes,” Databricks’ Kofoid says, to ensure you’ll remember everything later. “Use the guiding questions of ‘What may not work?’ and ‘Why shouldn’t I do it?’ This helps you avoid the problem of ‘happy ears,’” or confirmation bias, when the decision becomes largely emotionally driven. And, while pursuing diligence on framework elements, don’t be afraid to probe. “Double-click on ambiguous statements like, ‘Our board likes to roll up its sleeves and get involved,’” Heidrick & Struggles’ Peck says.

But “perfect data can still lead to surprises,” Zendesk’s Eggemeier says. Even if you take a comprehensive approach to diligence, it’s likely you’ll miss something. “You may see just the tip of the iceberg,” he says. “Things may be intentionally left out, but usually not to the point of negligence. More likely, they are selling people on the opportunity and are selective in what they share.”

Kofoid agrees: “There are shades of gray. Things can be spun, such as around product–market fit and competition.” Confluent’s Schultz says, “You could be misled on metrics like lead flows and attrition, but it could also be that things just change fast from the time you talk to the time you join.”

Or there may be unintentional omissions. “The company may not be mature yet on their journey, or they haven’t ever hired a leader for this kind of role,” Sprout Social’s Barretto says. “But the onus is always on you as the candidate.”

And be careful not to let optimism and emotion get in the way of objectivity. “It’s very easy to fall in love and not ask the hard questions—what can go wrong with the technology, team, culture? What failure modes might there be?” says Schultz. Kofoid adds: “People go in trying to sell themselves, but make sure it’s right for you. Feeling good isn’t enough.” He notes that this frequently happens when leaders follow others to a new company—they let their feelings cloud their judgment and often fall short on doing their full diligence. 

“Ego and positive framing can cause blindness to the reality of a business,” Peck says. “Listen to your instincts and inner voice, shaped by years of experience.” Critically, he also advises having your needs met before you enter the new role: “Role, compensation, anything promised—things often don’t materialize the way they’re supposed to after the fact. Like if they say, ‘We’ll bring you in and figure it out.’ Figure it out up front to avoid resentment on both sides. Departures are expensive for everyone.”

Now that I’ve stepped into the role, what should I prioritize to ensure early success?

The first few months in a new role can be the most demanding. You’re making decisions without full context, learning the culture, and building relationships—all while trying to deliver impact quickly. It can be a complex time even for seasoned leaders. 

Yet this early window also presents a unique opportunity. There’s typically more latitude to observe, ask questions, and experiment thoughtfully. It’s a time to listen actively, surface unspoken dynamics, and begin to shape your leadership approach. When you act with intention, the early days can be a powerful foundation for long-term credibility, trust building, and strategic influence.

“You’ll have a grace period of months at most, but not a year,” Databricks’ Kofoid says.

How best to spend that time? Start by listening. “Listen instead of coming in swinging,” Heidrick & Struggles’ Peck says. “Be careful about overindexing on proving yourself.” It’s also important to anticipate organizational dynamics, especially your potential impact on others. For example, as a new leader, you may own part of something, but that means someone may be losing responsibilities or influence. “Understand what it means for them,” Peck says. “If trust is broken early, it’s hard to repair.”

Alongside that sensitivity, though, it’s also important to trust yourself. “Walk right into the fires,” UKG’s Morgan says. “That’s how you learn.” Zendesk’s Eggemeier agrees: “I saw things to improve but doubted myself about making big changes early. I should have trusted myself and believed in two-way doors.” 

Some things may be easier than others as a new leader. Some less so. “You can muscle through the compensation plan,” Kofoid says. “But product–market fit might be harder to address.” 

And culture is a challenging area. “Tread lightly on cultural norms,” Eggemeier advises. “Be thoughtful and deliberate and see if you can work with them rather than changing them.” HR leaders may provide information about the culture, but they will generally be careful with their words, so it’s best to read between the lines where possible. Similarly, the head of product is also an important source but may be careful about “calling the baby [product] ugly,” Kofoid says.

As in the due diligence phase, get the information you need from within and outside the organization. “Ask questions of the team,” Confluent’s Schultz says. “Am I communicating well? Enough? What can we do better together?” Morgan says, “Jump outside the four walls to talk to customers, including those who are unhappy and those you lose. Customers contextualize everything.”

“Look for board members who complement your skill set, including independents who’ve run large organizations themselves,” Schultz says. “They’ve helped me understand how the CEO operates and thinks.”

But still, what if things aren’t going as hoped? “Be super honest before you own the problem,” Schultz advises. “Say, ‘This is how I’m going to be operating’ and solicit feedback. It sets you up for making moves later, including if you feel it’s just not working out.”

Perhaps above all, try to maintain perspective. “New hires often feel they hate it and need to get out,” Kofoid says. “But more often than not, it will work out. You can be talked off the ledge. You just have to get through that first year to reach more comfort and stability.”

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What if I'm hiring

Sitting on the other side of the table comes with its own set of challenges. The leaders we spoke with emphasized the value of authenticity in the hiring process.

Being direct and transparent, especially about the more difficult or less polished aspects of the role or organization, helps set realistic expectations. In fact, it often leads to better outcomes by ensuring candidates have a clear and accurate understanding of what they’re stepping into. Candor builds trust early and reduces the risk of misalignment down the line.

“Reveal all the skeletons in the closet,” Sprout Social’s Barretto says. “The things you think are broken and you need help with—see if these things excite them or scare them. Do some hypothetical situations.”

Zendesk’s Eggemeier says, “People you want on a turnaround are usually attracted by thorny issues or strategy points or people issues. Call out the elephants in the room as opportunities to solve things together. If you’re too positive, they may feel burned upon arrival.” 

An ideal scenario, in fact, is if a new leader arrives and thinks, “This isn’t as bad as they said.” That means giving them the lay of the land on fundamentals such as sales, productivity, and attrition, but also the softer elements such as culture.

At the same time, make sure to ask the tough questions of the candidate. “It’s easy to fall in love, but be objective,” Confluent’s Schultz says. That will help everyone understand if it’s a mutual fit.

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Conclusion

Exploring a new opportunity—whether you’re contemplating a move or already stepping into a new role—can be both exciting and daunting. But as the leaders we spoke with affirmed, the difference between a smooth transition and a rocky one often comes down to preparation.

Doing the work up front matters. That means deep diligence on yourself and the opportunity, talking to key stakeholders within and outside the company, and finding the right allies and information sources, among other tactics. But remember Tom Eggemeier’s advice: “Perfect data can still lead to surprises.” You may not be able to know exactly what you’re getting into, so remember that the best preparation includes remembering to expect the unexpected.

A thoughtful, intentional approach not only helps ensure the opportunity is the right fit but also positions you to lead effectively from day one. With clarity, alignment, and the right preparation, you can step into your next chapter with confidence—ready to contribute, build trust, and make a lasting.

Acknowledgments

The authors wish to thank the following executives for sharing their insights: Ryan Barretto, CEO, Sprout Social; Tom Eggemeier, CEO, Zendesk; Andy Kofoid, president of global field operations, Databricks; Jennifer Morgan, CEO, UKG; and Erica Schultz, president of field operations, Confluent. Their views are personal and do not necessarily represent those of the companies they are affiliated with. They also wish to thank David Peck, global practice managing partner of Heidrick & Struggles’ Coaching Practice.