In a thought-provoking conversation with Bestow’s Chief Revenue Officer, Lena, we raised the question: Should today’s executives act as coaches?
The discussion explores whether executives can or should take on the responsibility of coaching, how it affects team performance, and how it ties into company culture and growth.
Let’s unpack Lena’s insights on this vital topic impacting leaders in startups and large organizations. You can watch the full video interview here, but below is a comprehensive
Below is a breakdown of the key talking points from that discussion.
From Finance to Revenue Leadership
Lena, the Chief Revenue Officer at Bestow, brings a unique blend of financial acumen and strategic insight to the conversation. Her story begins in Ukraine, where she studied finance. From there, she entered the world of high-impact management consulting at PwC and McKinsey. These early roles laid a strong foundation for her analytical and strategic approach to business.
Eventually, Lena transitioned from consulting to working with technology and financial services companies. Her time at JPMorgan Chase was pivotal—she led the charge of building a tech-enabled platform from scratch. That hands-on experience became a proving ground for her future executive roles.
Later, she moved to Earnest, a fintech company, where she served as a General Manager. At Earnest, Lena was involved in day-to-day operations and was promoted to the executive team, where she was responsible for P&L and driving business outcomes.
Eventually, her path led her to Bestow, a company focused on transforming life insurance through technology. As Chief Revenue Officer, she was tasked with growing the company’s revenue functions, including pre-sales, sales, partnerships, customer success, strategy, and operations. She’s held this role for over three years, propelling the company forward.
Her wide-ranging experience gives her a practical lens through which she examines the role of executives, not just as managers or strategists but as coaches.
Should Executives Act as Coaches?
One of Lena’s most potent ideas is executives’ need to act as coaches (especially those in early-stage companies). She acknowledges that many leaders claim they “don’t have time” to coach. However, according to her, coaching is one of the most critical investments an executive can make, particularly in startups where alignment and execution are everything.
She compares an executive to an army general.
A general doesn’t just bark orders. They translate a high-level vision into actionable strategy and align troops (or, in this case, team members) toward a common goal. That level of synchronization doesn’t happen without coaching.
In early-stage companies, revenue leaders still have to be “in the field”—hunting for deals, refining strategies, and iterating on the product-market fit. Coaching may feel like a luxury when quotas are hit, partnerships are closing, and forecasts are building.
But Lena challenges that notion. She insists that executives must prioritize coaching despite these pressures.
The management style—whether entrepreneurial or corporate—can heavily influence how much coaching occurs. In rigid, corporate-style environments, coaching might be mistaken for micromanagement or viewed as a distraction. On the flip side, startup cultures often favor speed over structure, which can also deprioritize coaching.
Yet, regardless of the setting, Lena maintains that executives are responsible for coaching their teams.
There’s also a deeper issue: many seasoned execs, even those with B2B sales backgrounds, have never been taught how to coach. Their default mode is to command, direct, or “just do it myself.” Coaching, however, is a discipline. It requires patience, structure, and empathy. It’s about guiding, not instructing. And that mindset shift is essential for today’s executive leaders.
Mentoring Is Not the Same as Coaching—And That’s a Problem
One of Lena’s standout points is the critical difference between mentoring and coaching. Many sales leaders get promoted because they’re top performers. They closed the big deals. They hit 150% of the quota. And now they’re in charge of a team. But here’s the catch: success in sales doesn’t automatically translate to success in leadership.
These executives often know how to mentor. They can say, “Here’s what I did when I faced a similar challenge.” But that’s not coaching. Coaching is less about giving advice and more about asking questions, listening actively, and helping team members develop solutions. It’s a different skill set entirely.
And here lies the challenge for the current generation of leaders. Many haven’t been trained to coach. They may be inspiring or brilliant in their domain, but their approach to leadership lacks the tools that real coaching demands. This creates a gap between intent and impact. They want to help their teams succeed, but without coaching skills, they risk falling into patterns of control rather than empowerment
.
Coaching Your Top Performers, Not Just the Stragglers
Most traditional coaching programs focus on underperformers. It’s the squeaky wheel that gets the grease.
But Lena flips that idea on its head: Why not coach your top performers instead?
These are the people already delivering results. Extra coaching could double their output—from 110% of quota to 200%. That’s a much higher return on investment than trying to drag someone from 50% to 60%.
Lena’s perspective challenges the way we allocate our coaching energy. She suggests we stop trying to “save” every struggling rep and instead amplify the strengths of the best performers. That shift in focus could radically increase team performance and morale.
This strategy is also more scalable. Top performers already have the foundation, and they’re hungry to improve. Coaching them often yields faster results, and those results inspire others on the team.
Coaching Starts at the Interview Table
Coaching does not begin during a quarterly performance review. According to Lena, coaching begins during the interview process.
Executives can establish the tone for a coaching relationship by being transparent about the job, expectations, challenges, and the level of support available.
This honesty helps candidates self-select, increasing the chances of a strong fit. And when a strong fit exists, coaching becomes that much more effective.
Lena also discusses providing advice early on, recommending people to talk to, materials to study, and skills to focus on. All of this falls under the umbrella of coaching. It’s not about waiting for a formal session; it’s about creating a culture where development is constant.
She mentions the Krueger-Dunning effect, the idea that people tend to overestimate their abilities. This psychological nuance means executives need to assess candidates carefully during interviews. Some candidates may appear confident but lack the skills they believe they have, and others may undersell themselves. Effective coaching begins by recognizing these differences.
Moreover, Lena flips the interview dynamic. It’s not just about whether the candidate is good enough for the company; it’s also about whether the company—and the executive—is good enough for the candidate. Top performers want a challenge, but they also want a leader who will help them grow.
Coaching as a Talent Magnet
Finally, Lena explains how coaching becomes a competitive advantage in the talent race. The most sought-after candidates aren’t just comparing salaries or perks. They’re looking at the quality of leadership. They want to know: “Will this executive help me become a better version of myself?”
It’s not about making empty promises. It’s about offering real growth opportunities. That differentiates between a “maybe” and a “yes” when top performers decide where to work.
Executives need to ask themselves: What are we offering beyond compensation? Are we creating a space where talent can thrive? Are we coaching our people to unlock their full potential?
The best executives don’t just manage—they develop. In today’s talent market, the companies that win are the ones where coaching is baked into the culture, not tacked on as an
Afterthought.
In Conclusion
The conversation with Lena illuminates a transformative idea: executives must act as coaches if they want to drive real, sustainable growth. Coaching helps align teams, improves performance, and attracts top talent. It’s not a soft skill—it’s a business strategy, and we, as seasoned coaches, can’t agree more.
Whether you’re a startup founder, a CRO at a scale-up, or leading a team in a corporate giant, ask yourself: Am I spending enough time coaching? Am I building my coaching skills? Most importantly, am I creating an environment where my team can thrive?
To dive even deeper into Lena’s approach and insights, you can watch the full conversation on YouTube here:
