Careers

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Lori Anderson first went through one-on-one executive coaching when she took the helm of the International Sign Association (ISA), a group that had seen ongoing leadership turnover. Two decades into her CEO job, feeling unmoored after COVID-19, she pursued the experience again. Whereas that first coaching round felt nurturing as she developed her leadership style, the second experience had more of a tough-love tone. Both coaches, Anderson told CEO Update, were just what she needed at different points in her career.

Coaching sometimes begins after a company identifies behavior that they want an employee to adjust. Other times, it’s about a worker’s overall presentation. And some participants dive in when they see a need for growth in themselves.

“The reality is, all coaching is about driving change of some sort,” explained Ann Wheeler, a principal at executive advisory firm Odgers Berndtson in its U.S. Leadership Advisory Practice.

“Sometimes, an organization will sign someone up for coaching to help them learn different behaviors or ways of presenting themselves. A lot of people raise their hand for coaching because they’re interested in growth. They’re interested in taking on a role that is different than what they’ve done before or is expanded beyond anything they’ve done.”

Coaching is also a space to express ideas, including those that could muddy professional boundaries if an executive sought counsel from direct reports who might also be former peers.

“The closer you get to the top, the lonelier it gets, and having an external sounding board that you can talk to safely and isn’t going to run out and act on something you’re just thinking about can be very, very useful,” Wheeler said.

Whereas coaching once carried a remedial connotation, those working in the space, along with most who seek it out, now consider it an opportunity.

“I would say today, most individuals that engage in coaching are those individuals that really want to get to the next level and reach their potential,” said Robert Garcia, vice president of coaching in organizations with the Lexington, Ky.-based International Coaching Federation (ICF). 

Coaching for all

The idea of career and personal evolution as an underpinning applies to both one-on-one and team coaching formats. 

Executive coaching is typically for members of the C-suite. It’s a space, Garcia said, to discuss strategic organizational decisions or creative solutions to problems. Participants have an initial opportunity to share things they want to work on; then the conversation flows through related needs.

“There’s an agreement, and then it’s exploring the conversation and guiding through the process of coaching if there is something the individual needs to think about or talk through,” Garcia said.

Team coaching, on the other hand, centers on cohesiveness and alignment, Wheeler said. It’s not about helping others understand one person’s point of view but rather guiding the team to connect in a way that aligns members as a whole.

Team and executive coaching often coexist, Wheeler said. It’s sometimes necessary in team coaching to work individually with group members to meet their needs as their perspectives shift, she explained. These shifts often occur as individuals consider the overall needs of their departments and determine their own responsibilities within the context of an entire enterprise. In this way, team and executive coaching can provide simultaneous growth opportunities, so organizations shouldn’t necessarily home in on one format and exclude the other.

“It’s not an either/or,” Wheeler said. “It’s the both/and.”

Team coaching duration depends more on the length of projects, Garcia said, and can last as little as three months. Executive coaching often lasts six months to a year or longer. An executive could renew the experience at the end of an appointed time, or they might decide to maintain an ongoing relationship with a coach, Garcia said.

For executive coaching, Wheeler sometimes sees shorter timeframes of around three months of intensive engagement in which a participant might be preparing for a new role. But like Garcia, she said real behavioral change takes six months to a year. Coachees may start out with more frequent visits that spread out over time. 

The typical one-on-one meeting frequency is weekly, but Wheeler has seen clients more often if she’s helping them stabilize a crisis.

Choosing a coach

The prospect of coaching, Wheeler said, holds “a myriad of possibilities.” Whatever the area of intended improvement, it’s important to find the right fit for the situation and to select a coach who can be a partner and deliver when it comes to goals.

“Make sure that if you’re considering a coach, you understand what that coach tends to focus on, and is that a good match for what you’re looking for?” Wheeler said. “And don’t be hesitant to shop around.”

Wheeler’s background in marriage and family therapy set her up with an existing skill set when she decided to “retread” her professional life 25 years ago and use her assessment abilities in an organizational context. Although her initial training was not in coaching, she has refined her skills over the years through continued education. 

Today, Wheeler sometimes sees “chemistry calls” between executives and prospective coaches. This method helps in setting up a match in which coachees feel comfortable, she explained. It can be helpful to find a guide with a similar professional background who understands lingo and shares a certain knowledge bank, she said.

From a coach’s perspective it’s important to remove their ego from the equation and recognize when a match is not right, Wheeler said. In that case, helping a client find a new coach may be appropriate.

Results: What to expect

When it comes to results participants should expect to see from coaching, both experts agree the outcomes depend on the circumstances.

In a broad sense, success represents a shift in understanding approaches and setbacks; it can include the development of additional tools for forward movement in an existing job or toward promotion, Wheeler said.

“I think it looks like someone who’s starting to think about themselves and their world a bit differently, so they’ve got a different perspective,” she said. “You’ve helped open some doors for them, either in their mind, or their eyes or in their heart.”

An exploration process that might not otherwise have taken place and an increased level of satisfaction are often indicators of a successful experience.

“At the end, it’s taking a great opportunity to really talk about getting to the next level — being happier,” Garcia said.

Positive experiences with coaching at the C-suite level can result in a trickle-down effect to other organizational tiers. “Lots of organizations are recognizing the impact that coaching is having and want to build more. It typically starts with executive coaching,” he said. “And then, you see how it permeates throughout the organization. . . . Everyone should benefit and really reap the benefits of coaching.”

In his work with the ICF, Garcia oversees efforts to help entities that may have ties with external coaches to build capabilities internally and “create a coaching culture,” with leaders of organizations applying what they learned from coaching in their work.

“We’re developing programs around leaders using coaching skills,” he said. “So, not only are the leaders getting coached, but they are using coaching skills to become better leaders: asking better questions, listening more. The core competencies of coaching are being used. 

“They’re not coaches, but they’re using coaching skills to be more effective leaders.”

‘I don’t know if I would have made it’

When Anderson took over at ISA in 2004, she was the organization’s fifth CEO in six years. And she was coming in with no CEO experience — she’d never led a board of directors or helmed a sizeable staff. She knew, given the turmoil the organization had faced, that she’d need an adviser.

She enlisted help from a coach she’d met at an industry event who initially performed an evaluation of her leadership style that included others’ perceptions of her. Anderson said that feedback was “eye-opening” as she began her CEO journey. As a result, Anderson said she felt increased self-confidence and had a better understanding of her own communication style and the modifications she could make when addressing different team members. She worked for about six months with that coach and considered the experience a lifeline.

“I can honestly say that I don’t know if I would have made it if I hadn’t had this trusted person, who was an unbiased third-party confidant, because I needed to know how to position myself as a first-time CEO to boards, to the public, to the members, to the staff,” she said.

In 2023, as the business world was still slowly emerging from the clutches of COVID-19, Anderson found herself thrown off balance. The pandemic demanded a new type of leadership from her — one in which leaders everywhere were making unprecedented decisions.

“It was a very traumatic time,” she said. “I felt like I had a bit of PTSD, and I felt I had lost my moorings.”

Outside guidance, once again, felt right to her, and she reached out to friends and colleagues for advice on selecting another coach. This time, she looked for someone who had coaching credentials or who had turned the endeavor into their full-time career. Whereas her first coach was more of a “nurturer,” Anderson said her most recent selection turned out to be “more of a slap.” The more direct style, Anderson said, felt appropriate.

“There were some fundamental changes that needed to happen in the organization and with my style, and she was instrumental in helping me navigate some really tough structural issues that needed to be addressed,” Anderson recalled.

She came away with an ability to make quicker decisions and avoid prolonging processes. Both coaching stints, however, allowed her to address an ongoing tendency: conflict avoidance.

“Some people are just drawn to having difficult conversations, and that just isn’t me,” she explained. “Each coach worked with me on how to better internalize that feeling and understand that it’s a perception, not a reality.”

Garcia’s idea that coaching culture can permeate organizations is evident in Anderson’s takeaways. She has recommended coaching to staff at all levels, and she’s seen it provide unique benefits. She described a situation in which a team member struggling with getting organized worked with an ADHD coach to better navigate their work environment.

“Our workforces are neurodiverse. There are coaches who can help in all levels of this,” she said. “Executive coaching isn’t just for the top executive. It’s for every member of the team.”

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Making the switch from leading a small to a large association might seem daunting. Budgets are bigger, the staff is larger and strategic plans are executed by more teams. But CEOs who have done it say the same basic rules of leadership apply to both types of groups.

Boards and search committees at large associations (those with annual revenues upward of $12 million) want to see CEO candidates demonstrate baseline competencies: leadership, strategic planning and execution. 

Plus, the entrepreneurial spirit that CEOs exercise leading small associations (those with annual revenue of less than $5 million) translates well, especially when the unexpected happens and the organization needs to quickly change course. 

CEOs Shawn Boynes, Linda Darr, Linda Caradine-Poinsett and Veta T. Richardson all made the leap to large associations, reveling in the excitement of new challenges and overcoming obstacles without looking back.

Opportunity knocks

Shawn Boynes wasn’t looking for a new job when a recruiter approached him about the CEO position at American Counseling Association (ACA). But he always takes time to talk to recruiters, and five people happened to recommend him for this opportunity. 

At the time, he was executive director of the American Association for Anatomy (AAA) in Bethesda, Md. In nine years, he’d transformed the 130+ year-old organization into a modern and more relevant scientific association. He and the board had revamped its antiquated governance system and introduced innovations that led to the creation of a forward-thinking DEI effort. Boynes was AAA’s first Black CEO and because of his team’s efforts, AAA had elected its first Black woman to the board.

Yet, the more he spoke to the recruiter, the more excited he became about the CEO role at ACA. 

“I resonated with the mission of the organization because my mother suffers from severe mental illness,” he said. “To be in a position to lead an organization focused on mental illness, I was just energized by it.” 

Boynes joined ACA as CEO in July 2022. His association background includes a variety of sectors — health care, science and legal — but he didn’t have specific mental health experience. “I didn’t want to pigeonhole myself into one industry and functional area,” he said. “I wanted a broad base of experience to help keep my skills sharp. It served me well in each role and at this point in my career, prepared me to lead an organization of this size.” ACA has 60,000 members, compared to AAA, which has 2,000. 

Boynes’ change management experience and strategic vision stood out to the board. “I moved to the next step in the process because that recruiter believed in me,” he said. For many years, Boynes felt a lack of access to opportunities. “I think sometimes recruiters look for candidates that fit into a particular box,” he said. “You fit the criteria but you just haven’t worked in a larger environment and the difference is scale. Specifically, for me, I had lots of receipts that I could pull out and speak to, ‘Here’s what I’ve done, and here’s how I did it.’” 

Opposites attract

Linda Darr was a finalist in a CEO search for a different trade association when the American Council of Engineering Companies (ACEC) contacted her about its top job. She interviewed with the Washington, D.C.-based association on a Thursday and they offered her the president and CEO position that Monday. 

“I had little time to prepare,” she recalled. “But you know when you’re connecting, and what you’re saying resonates with people. Engineers are generally introverts. Most of them have poker faces. (But) they were nodding their heads and smiling” during the interview.

Darr, a CEO Update Roundtable member, joined ACEC in August 2018, leaving behind her CEO role at the American Short Line and Regional Railroad Association. She spent most of her career in transportation and infrastructure, which caught the hiring committee’s attention. Much of ACEC’s focus is related to that sector. 

Not being an engineer helped, too. “With engineers, they needed somebody that would speak to them in more of a bold way than they were used to,” Darr said. “I’m nothing if not bold. When I was in second grade, I jumped off the high dive without knowing how to swim. Luckily, I had two sisters at the pool to save me and pull me out of the water.”

While jumping into to her new job, she didn’t require saving. “I inherited an amazing team,” she said. “From that perspective, you can go so much further, faster. There wasn’t as much ‘cleanup in aisle three’ with this group.” 

Even so, the most important transition is with the team, Darr said. “I told them what they can expect: ‘Here’s the good and bad of Linda. Here’s what my expectations are for the organization and here’s how we’re going to go about doing it.’ If you don’t tell them, it’s going to take a long time for them to figure it out. They’re better off knowing at the jump.”

Darr is excited by the intensely collaborative, problem-solving nature of engineers and their mission of designing solutions to important problems like climate change, hunger and mobility. ACEC was her third time in the top job in a career that spans almost 20 years. Based on her experience, she said the two most important parts of any transition are to never stop listening and to act. 

“They (the search committee) want to see something happen and see it happen soon,” she said. “The challenge is to know when to act. You cannot upset the applecart too much from day one, but you have to have clear, visible change. Moreover, you need to be nimble. Really listen and make sure the plan you put in place is reflective of the day’s problem.” 

Change lanes

Linda Caradine-Poinsett was CEO at the American College of Prosthodontists when a colleague suggested she’d be a good fit for the top job at Institute of Real Estate Management (IREM) in Chicago. Poinsett joined IREM as CEO/executive vice president in June 2022, bringing more than 20 years of experience in different sectors of association management to the role. 

“It was an example of someone seeing your skills and understanding what you bring to the table irrespective of the industry you happen to be working in,” Poinsett said. She has a background in leadership development, governance and finance. Still, she calls her first association fundraising job in the early 2000s, which involved collaboration, networking and relationship cultivation, the primer for every subsequent role she had.

Throughout her conversations with IREM’s search committee, their shared values of leadership, collaboration, integrity and inclusion echoed loudly. So did her experience meeting change, devising ways to help organizations grow, and understanding membership’s importance to growth and the board’s fiduciary responsibility to members. 

Poinsett recommends that CEO candidates approach the interview process as if they already have the job. Familiarize yourself with the organizational chart, discover where the organization is within the strategic plan and learn about team members. It will prepare you to ask the right questions and gain a deeper understanding of the organization, team dynamics and the board.

Boomerang back

When Veta T. Richardson joined the Association of Corporate Counsel (ACC) in 2011 as president and CEO, it was a proud moment. She returned to the Washington, D.C.-based organization, where she was first a director and later vice president, after a decade away to replace her mentor, Fred Krebs, who was retiring. 

Richardson came from an executive director position at the Minority Corporate Counsel Association (MCCA). While both associations have a similar focus on the corporate legal executive, as well as overlapping memberships and boards, MCCA is small and ACC, large. 

“ACC was looking to transform and grow, achieve a global reach as opposed to U.S.-centric, and roll out new technologies to improve services,” Richardson said of why recruiters contacted her. “My track record for being entrepreneurial and growing strong brands helped me stand out.”

That track record included opening up new revenue opportunities at MCAA. Richardson disrupted an outdated business model, expanded the stakeholder base, and implemented a turnaround strategy to go from financial distress to profitability — positioning it as a market leader.

Despite her history with ACC, Richardson could not presume she knew the organization. It had changed fundamentally in 10 years. Her first priority was focusing on the internal team: listening, getting to know staff, hearing their thoughts, understanding their roles and assessing team competencies and strengths. Equally important, she wanted them to get to know her as a leader and understand that she believes, like Krebs, that people are an organization’s greatest asset. 

Her second priority was meeting the global board of directors and leaders of ACC’s regional stakeholder networks, to hear their perspectives about how the association was meeting their needs. The conversations helped her identify opportunities for improvement and early wins —the visible change that Darr mentioned — to give everyone confidence in her as a new leader. 

Her third priority was meeting external partners and stakeholders, to keep them engaged and analyze gaps or opportunities to offer additional value. 

“The most important thing as a leader is to make sure you’re a net giver,” Richardson said. “Giving and helping others through their challenges makes you more adept to handle the issues that come your way. If all I attempted to solve is what I experienced, I don’t think I would have been as good at it.”

Change takes time

Poinsett said it can take up to two years to get a handle on how an organization ebbs and flows, particularly managing a larger staff. 

“In a smaller organization, you’re closer to the execution phase of work on projects. You can see it in real time, where the inefficiencies are happening, and course-correct sooner. In a larger organization, you’re further removed and don’t see the inefficiencies right away, especially when it’s integrated across multiple departments. To identify who really owns the project or strategy is one of the challenges going into a larger organization.”

Another issue is keeping track of where the organization is in its multiyear strategic plan. Sometimes, objectives carry over year-to-year, overwhelming staff with work. 

“It’s important to be mindful of the impact trying to meet those different goals is having on the team,” Poinsett said. “It’s OK for an executive to say we cannot handle that, or I need some help with prioritizing where we need to go. At the end of the day, I’m finding that if the team is not happy, they’re not able to execute on the strategic plan.” 

With bigger budgets come more resources, and that’s a game changer. Having more staff to lean on has been thrilling for Boynes. “Working in a smaller staff environment, I didn’t have a department. I had people,” he said. “I have departments now. I have my direct reports who are all chiefs and they all have direct reports. You can delegate more. A small staff environment is a different hustle. You have to make sure you have your finger on the pulse of all things, at all times.”

Darr can relate and advises letting go of work once it’s delegated. “You have to hire the best people and let them run it,” she said. “Check in with them, rein them in now and then, and actively communicate. But give them the space to run it. You don’t have to do it all yourself.” 

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