Megan O’Connor, the cofounder and CEO of education startup Clark, got her first taste of professional coaching when she joined the Human Ventures startup studio. “Sometimes you do these things because you think you’re supposed to,” O’Connor says, “like getting a coach, or listening to the Reid Hoffman podcast.”
But meetings with her coach turned out to be surprisingly insightful. “What [coaching] has actually produced has far exceeded my expectations,” she says. “I’m an evangelist for it now.”
For a time, executive coaching was either a remedial solution for companies that needed to right the ship, or the purview of the most influential CEOs. The late Bill Campbell, for example, famously coached figures like Steve Jobs and Larry Page. “Coaching used to be a bad thing,” says Alex Pascal, the founder and CEO of coaching software startup CoachLogix. “Now if you don’t get a coach, you kind of don’t want the job anymore.” As more venture capitalists preach the value of coaching, a one-day coaching session organized by an investor can be a gateway to full-time coaching for even the reluctant founder. “A lot of us have worked in and around startups and seen great and not-so-great cultures firsthand,” says Laurel Woerner, who helped put together a group coaching program at RRE Ventures. “Leadership can make or break a company regardless of how great the tech is or what the market opportunity is.”
Leaders of all stripes have increasingly turned to coaching, sometimes at the urging of investors who have seen poor leadership and toxic work cultures tank sky-high valuations at a number of companies (the latest being WeWork). Gone are the days where people idolized the ruthless CEO perpetually holed up in his corner office. “Some people think you have to have a crazy personality to be a founder, or have to be slightly eccentric,” says Human Ventures founding partner and CEO Heather Hartnett. Enter the affable CEO who sits amongst her employees and has an open-door policy.
The business coaching industry is on track to be worth $15 billion this year, according to IBIS World, as compared to just over $9 billion back in 2009. Now, a coach is one part prestige signifier and one part self-optimization tool—the goal being to become a better leader, certainly, but also a more empathetic, introspective version of yourself. “It’s been popularized by podcasts and some coaches who are [known] in the media,” says executive coach Alisa Cohn, who has worked with companies like Venmo and Etsy. “I would say it’s a perk and in some cases, a status symbol.”
And it’s not just CEOs and executives who are seeking guidance. Though coaching doesn’t come cheap—many charge tens of thousands of dollars for just a few months—organizations like Bravely and BetterUp are democratizing it, expanding coaching beyond the executive ranks at a lower price point. As career trajectories have shifted, millennial workers are especially invested in their personal and career development, whether that means tracking their sleep or seeking out a coach. “Millennials tend to be very development-oriented,” Pascal says. “You want to think about your career proactively. We’re [no longer] in this stage where you’re going to have a 50-year career at one company.”
The value of coaching
Some founders and CEOs may turn to coaching when they’re faced with a specific hurdle or some sort of interpersonal conflict—often, drama in their executive ranks. “In a startup environment, there’s a lot of friction with the people you work with—it’s just the nature of the environment you’re in,” Pascal says. “Founders just don’t have the time or tools to properly diagnose what’s going on.”
In other cases, the catalyst is change: A new CEO may be struggling to adjust to her new role. For O’Connor, consulting with Peter Shallard, a venture partner and in-house coach at Human Ventures, was a key part of how she navigated her company’s recent acquisition. “When you’re going through an acquisition, things change day to day, or even hour by hour,” she says. “[Peter] rode the wave with me. We did daily updates, even if it was just on Slack.”
Many CEOs and founders are simply overwhelmed and looking for a judgment-free zone. A venture capitalist is literally invested in a founder, as is a cofounder; a spouse or friend may lack context. A good coach can be impartial and blend business savvy with emotional intelligence. “It’s that feeling of, ‘oh my gosh, I can’t do all this on my own,'” says Amy Eliza Wong, who describes herself as both a life coach and executive coach. “Sometimes, it’s just the stress of running a company and worrying that they can’t even identify what the important things are.” Some women founders, Wong says, come to her with issues specific to how they’re perceived as female leaders. The most common refrain? “I need tools to appear assertive without being bitchy.”
When it comes down to it, what most leaders are really after is deepening their empathy and improving their communication skills. The very skills that might make a leader successful from a business perspective—being ruthless and uncompromising—may not broker healthy relationships with employees or ensure the long-term success of a company, especially in today’s workplace. (The harsh Jobsian approach, for example, might not be palatable in 2019.)
Plus, as Shallard notes, there’s a business case for empathy even beyond the merits of a positive work environment. “Empathy is one of the most underrated game-changing skills for anyone to have, but certainly for entrepreneurs, it’s absolutely critical,” he says. “One of the reasons I think empathy is so important is because being able to achieve product-market fit at an early stage startup has a lot to do with a founder’s ability to place themselves in the customers’ shoes and ask themselves, ‘What does this person care about that I do not? What does this person want that I do not?'”
This business case also explains why investors are putting their money behind coaching—offering an introductory session in-house, for example, or supplying founders with a pool of vetted coaches. At Human Ventures, that takes the form of a “self-awareness accelerator” conducted by Shallard. “The number one thing that destroys early-stage, fast-growth companies is hubris, cognitive biases, and blind spots,” Shallard says. “The founder doesn’t really know how their own brain works.”
Even leaders with a cofounder benefit from a coach, Hartnett says, perhaps even more so than sole founders. That’s where Shallard’s work as a coach has paid off, quite literally—in mitigating the financial fallout when cofounders have gone their separate ways. “Peter has been instrumental in identifying problems with cofounders before they even knew there was something coming,” Hartnett says.
What coaching entails
To get a sense of a client’s skill set, many coaches start with some sort of evaluation, like a personality assessment or 360 review, which involves gathering feedback from other employees. “I’m a big fan of evidence-based psychology,” Shallard says. “One of the areas where there’s a huge body of research and literature is the Big Five personality trait system. So that’s a tool we rely on heavily.” Shallard says the Big Five assessment also helps founders gain a better understanding of past relationships. “I spend a lot of time with these founders talking about their history and how things have gone in the past, because typically this isn’t the first thing they’re doing,” he says.
The coaches at RRE Ventures do a listening tour at founders’ companies and encourage founders to write a “user manual” detailing, for example, their work habits or the things that bother them. “The idea is you write a user manual for yourself, the same way you do for a washing machine, Woerner says. “We’ve had people go back to their teams internally and do those same exercises.” Liz Tran, the founder of executive coaching studio Reset, uses the Hogan Personality Inventory, an assessment that evaluates and scores strengths and weaknesses, along with key motivators and values.
One of the most vaunted features of Chief, a private club for female executives, is its Core Group—peer coaching that she describes as “executive coaching on steroids.” Like Tran, Chief cofounder and CEO Carolyn Childers found that a one-on-one relationship alone didn’t quite cut it because a coach couldn’t always have the necessary context. “There’s an executive coach in the room, so you still get the coaching element, and you get somebody to facilitate that, but you also have up to 11 other individuals in that room who understand your context,” she says. VC firms like RRE Ventures have also found entrepreneurs respond well to group coaching for this reason.
Other organizations like Collective Gain take an unorthodox approach approach to coaching, even incorporating astrology workshops into their work with companies. “At the end of these [workshops], people say they had a good time, and they learned something about themselves,” says Lizzie Alberga, the founder and CEO of coaching organization Collective Gain. “[Even] the executives say they have a whole new respect for astrology and how it can be strategic in the workplace.”
Jonathan Fader, a clinical psychologist who used to work primarily with athletes, relies on a technique called motivational interviewing. “What people tend to do is tell [clients] what they need to change and how to do it. That doesn’t really work because there’s no connectivity and empathy and engagement.” Motivational interviewing, on the other hand, helps people come to their own conclusion about what they need to do differently. In his work with CEOs, Fader often hires actors to play-act scenarios with his clients. “The process is that the leader generates a vignette based on a pain point or a point of friction, or based on something they just want to improve,” Fader says. “Then I train the actor to portray that. My feedback is helpful, but it’s almost sometimes more helpful to get feedback from the actor.”
As a CEO, this sort of personalized feedback can be hard to come by unless you explicitly ask for it. “Most motivated people want to be working on themselves,” says Karson Humiston, the CEO of Vangst, a recruiting platform for cannabis jobs. “But you can only read so many books that are so generalized. Coaching is so specific to you.”
When Humiston first got a coach, one of the initial steps was a 360 review. Humiston asked her employees to be “brutally honest.” “I said, ‘Tell me all the things I suck at, and I’ll work on them,'” she says. “People were honest. I loved it. As a founder, you have all these people working for you, and you’re giving them performance reviews, but nobody ever really gives you feedback.” As her company has grown—from 20 people two years ago to more than 80 today—coaching has proven helpful to communicate changes internally to early employees. “Advisers and investors can help you get connected with amazing talent,” Humiston says. “A coach can help you frame the story to the team about the people you’re bringing in.”
Some founders, she says, make the mistake of engaging a coach just to check a box. To get as much as she could out of the experience, she says, required a significant commitment on her end. “It’s just as much on me to put the time and energy into this relationship as it is on the coach,” Humiston says. “I really laid it all out there. I invited the coach to the office to meet the team; I had multiple dinners with her. I said, ‘If we’re doing this, I really want you to know me as best as you can.'” The fact that she invested time and money in coaching itself shored up good will with her employees, Humiston says. “Multiple people on the team have told me they appreciate that I’m doing this,” she says. “It sends a message that you accept you don’t know everything.”
It also shows her employees that she wants to hear from them and understand their perspective—a key to opening lines of communication and building empathy. “You can’t feel empathy for someone if you don’t have a connection with them,” says Alberga. “It’s something you feel by listening, by being inquisitive, by showing up and being present without your own agenda. Only then do you build connection. If you’re an executive who’s only looking at how to drive the business and not connecting with your people, you can’t have empathy.”
Many of the exercises and tools coaches have in their arsenal—even the ones that might seem a little extreme—are ultimately in pursuit of cultivating empathy in a founder, whether that’s directed at their executive team or, in the case of a large Fortune 500 company, subordinates they may never meet. It’s all the more important given CEOs are often alone at the top, a point everyone I spoke to cited as a catalyst for coaching. “It’s hard to be honest about the roller coaster that you’re on,” says Sean Black, the founder and CEO of real estate startup Knock. “It’s a little bit easier when these coaches can absorb some of that.”
That’s why Shallard recommends that founders cultivate other meaningful relationships. “The biggest challenge entrepreneurs face is probably isolation,” Shallard says. “A lot of people come at this with an assumption of, ‘I have to do this on my own.’ I advise my clients to stack as many relationships like mine as they possibly can.”
Coaching may be a form of insurance for investors, especially given the trajectory expected from venture-backed startups. But it’s also an acknowledgement of the increased pressures on leaders—and a ballooning intolerance for bad behavior. “It’s a huge responsibility,” Hartnett says. “When you have a really fast-growing company, you have to now be aware of so much more. You can’t get away with some of the things that companies could get away with prior to #MeToo, prior to some of the environmental issues we’re facing. It’s only going to be a larger and larger responsibility.
The evolution of coaching
Of course, reaping the benefits of coaching hinges on finding someone who’s the right fit. That can be tricky given the coaching space isn’t regulated. (Some coaches do get certified through organizations like the International Coach Federation.) Unlike with psychotherapy, “there’s no requirement to be a coach,” says Eric Pliner, the CEO of leadership firm YSC Consulting. “You could get off this call and say you would like to be an executive coach. So absent a real design around the purpose of the coaching, and tying that to the business goals, it can feel like a risky or less valuable proposition.”
As demand for coaching has increased, so too has the supply. There is no shortage of coaches, whether you’re looking for counsel on a career transition or seeking more specific help with conflict resolution. Many coaches I spoke to concede the space is oversaturated and that those who seek out coaching should both be discerning and understand they may not find a match right off the bat.
The lack of regulation means coaches trade on experience and clientele and often find business through referrals. Former venture capitalist Jerry Colonna, for example, is one of the most sought-after coaches for the tech set. “Of course I wanted to hire [Jerry], and so did everybody else,” Black says. “We couldn’t get him for months, so it just never happened.”
Founders and CEOs tend to gravitate toward executive coaches rather than life coaches, though each coach offers a personalized approach. “If it’s strict executive coaching, you’re coaching a leader to meet certain business objectives or organizational goals—they’re going to use those as measures of success,” Wong says. But to accomplish those goals, she says, you may use some of the same techniques as you would with more holistic life coaching, for example. “Executive coaching and life coaching can really look and feel very similar.”
Even within executive coaching, the approach can vary widely depending on the coach in question. “Campbell had a testosterone-infused Silicon Valley kind of model,” investor Fred Wilson told Wired, comparing Campbell’s coaching style—informed by his years coaching college football—to that of Colonna’s. “Jerry’s model is more Buddhism and less football.” Gimlet Media CEO Alex Blumberg, one of Colonna’s clients, described him as woo-woo on a recent episode of his podcast, Without Fail. “Jerry’s woo-woo-ness takes many forms,” Blumberg said. “He hosts executive retreats where it’s not unusual for participants to play with clay or talk to plants or read poetry aloud to one another. And weep. There’s lots of weeping.”
The explosion of the industry speaks to the fact that coaching is not one-size-fits-all. Tran started her own coaching studio after concluding that there weren’t enough coaches with the right sort of experience—her takeaway from working with countless coaches at VC firm Thrive Capital. “I think a lot of people come to coaching because they’re working on their own personal growth story, as well,” Tran says. “This is the archetype I saw with coaches a lot: ‘I was doing this job at Google, and I got really burnt out, so I started taking care of my personal well-being, and then I decided to become a coach.'”
That might work for some people, but for founders, Tran believes it helps if a coach has a certain type of background—be it an entrepreneurial venture or operating experience—and distance from their own career journey. “I think it’s really, really hard to coach someone unless you had hands-on experience or have coached people in that area,” Tran says.
Whoever your coach may be, O’Connor says the most important thing is being committed to the process. “My mom once told me, ‘Never date a man who isn’t doing the work, aka in therapy, getting to know himself,'” she says. “I would say the same thing for people in the startup world. Don’t invest in or work for someone who isn’t doing the work.”