First Signals

Claire Kennedy was in high school when a teacher caught her making the wrong choice for the right reason.

The class was about to take a test. Students had been allowed to review their study materials until the test began. When everyone was told to put their materials away, Claire kept hers out.

There are plenty of ways a teacher could have handled the moment. The simple version would have been consequence: name the behavior, punish the behavior, move on.

But at that moment, her teacher took a different path. She pulled Claire aside and gave her what Claire still remembers as “such a powerful speech about what she saw in me.” She saw the pressure underneath the action, the ambition behind the bad decision, and the person Claire might become if someone showed her a different path to the same high standard.

She nominated Claire for an academic program for top students that took Claire out of her hometown and to Columbia University and Georgetown University with other top-performing 15-year-olds from across the country and around the world.

It was the first time she remembers being placed in a room like that and thinking, maybe I belong here.

A few years later, it happened again. Claire interviewed for a full college scholarship with Wayne Waddell, a then Louisiana Congressman. The conversation lasted several hours, and Claire couldn’t help but notice how he pressed her less on what she wanted to do and more on what she believed. She realized at that moment he was evaluating her for her character, not her ambition. She received the scholarship.

Wayne became a close friend and mentor and remained a huge influence on her life until he passed away last fall. For years, she wrote to him whenever she accomplished something or had an experience she thought would make him proud. He became something close to an honorary parent.

Before Claire fully saw herself, powerful figures in her life told her they believed in her and showed her what high character looked like. They helped her see she belonged on the climb with them, and off she went.

Claire spent much of her career, until recently, in Human Resources (HR). Because HR is a horizontal function, it offers a rare view into the inner workings of every part of the company, including which leaders show real character under pressure and which ones start to flail.

For Claire, leadership comes back to the type of character she observed in her early role models. Her definition is simple: “character is a commitment to values under pressure.”

Values are to throw on a wall or a website, but character shows up when there is a tradeoff, when the easier path is available, when winning faster means compromising something you claimed to care about. In her view, High Slope Talent cannot be separated from the moral choices people make under pressure. How you get to the top is more important than getting there. 

Extreme Tenacity

When Claire talks about herself through the PEAKS framework, she starts with persistence.

“The number one quality in anyone who is successful in any capacity,” she said, “is  perseverance."

Listening to her, it becomes clear that persistence is a skill she practices in sequence: define the problem, acknowledge what she needs to do, and drive into her second named spike around action orientation. 

Once Claire gains conviction, she values action over continued evaluation. She understands that you learn more from doing, and understands that pursuit of perfection and/or inaction are often the real challenge to some progressing towards their goals.

The third trait, and the trait that I see most clearly within her, is the one that gives the other two their shape: emotional grounding.

Without emotional grounding, persistence looks like “bull in a china shop” force and action orientation looks like flailing. Claire’s advantage is that she moves quickly from a place of deep self awareness and deep self management. She can name what comes naturally, what does not, and what she plans to do about it.

Systems thinking, for example, is not the first tool she reaches for. She has built that skill through discipline because her work required it. Her self-awareness keeps the gap from becoming an excuse. Her persistence keeps it from becoming a ceiling.

“A problem well defined is half solved,” she said.

That sentence shows up again and again in how Claire thinks. She uses her deep sense of self awareness and character to effectively define and get to the root of a problem, and from there she has enough momentum to solve it.

Feedback and a Long Drive

In 2020, as the world was falling apart with a global pandemic, Claire decided to travel across the country and spend her time in Wyoming.

She told her then CEO and mentor she would leave at 7 in the morning for a three-day solo road trip. At 7:05, her phone rang. It was her CEO.

“I just figured this would be a good time to give you some feedback while you’ve got a three-day solo journey across the country to think about it,” he told her playfully. He went on to explain, without mincing words, that Claire had developed a habit of telling people how busy she was. It was 2020, and everyone was underwater, everyone was in a tough spot. This verbal habit wasn’t helping her, if anything, it made her appear less self-managed, less mature, and more scattered than she really was.  

That kind of direct delivery and timing would shake most people. Claire described the feeling as relief. 

“As soon as you know what someone thinks about you and your performance , it’s such a relief,” she said.

Most people do not experience feedback that way. They hear critique and immediately turn inward. Am I failing? Do they hate me? Is my job at risk? It can lead to fight (get defensive) or flight (withdraw or spiral). Claire’s reaction is different because she has the emotional grounding and the capacity to truly believe that clarity  is kindness and feedback allows her to kickstart her action-orientation. Evolution is the goal, not perfection. 

“Not knowing where you stand and not knowing where you’re falling behind,” she said, “is a murky, very uneasy place to be.”

In other words, once someone names the thing, you can do something about  it.

She appreciates direct, no-nonsense feedback delivered by someone she knows believes in her. “Honesty without tact is cruelty,” she shared. The best leaders in her career have been direct without being careless. They challenged her while making it clear they were rooting for her. This was the heart of the manager and leadership training Claire developed as an HR leader. 

Her reaction to the Wyoming call says a lot about her coachability.  Nothing is permanent, energy is best spent evaluating a path forward, and once you define a problem, you can solve it. 

Career Turn

About a year ago, Claire made a career change from HR executive into Executive Search leadership where she helps VC and PE funds build out their portfolio companies' Executive teams.

She had reached a point where her HR leadership work was no longer getting the best of her. She felt drained and plateaued, but instead of jumping into a new opportunity, she took a thoughtful pause. She asked herself, “is this a patch or a pattern?”.

A patch is a hard season, a bad project, a company moment, or  temporary place . A pattern repeats often enough to tell you something about fit or sustainability.

Claire realized she was looking at a pattern.

“I believe very firmly in driving your own car,” she explained. Other people can support your journey, but you’ve got to define the path yourself and clearly articulate it to others to enable them to really help you. 

She sought support from her closest friends and mentors, a new therapist and a career coach. In other words, she did her own deep diagnostic work before asking her wider professional network to help. The order was important: she knew if she couldn't articulate her challenge and her goals, her network couldn't support her journey.  A problem well-defined is half solved. She
did not want to hand someone a vague sense of restlessness and ask them to solve her life.

Career Change Checklist

Claire’s career-change process can be turned into a practical checklist for anyone trying to use a network during a career transition. She outlined it in hopes it can support others deciding if they are in a patch or a pattern, themselves. 

1. Collect the data. Run your own 360.

Before you ask anyone else for advice, build a clear inventory of yourself.

Ask:

• What am I naturally good at?
• What do people reliably come to me for?
• Where have I failed more than once?
• Why did I fail? 
• What gives me energy? What feels truly inspiring? Who inspires me? 
• What drains me, even when I am good at it?
• Which skills do I want to build, and which ones am I tired of forcing?
• What journals, emails, performance reviews and 360’s can I reference for an honest reflection? 

Reflection and meditation must precede action for one to come to the best outcome.

2. Name the season.

Careers have seasons, and what served you last year may no longer be true. As the other aspects of you evolve, your achievements have evolved, so do your motivations. (Pro tip: to help name your season, consider which career archetype fits best). 

For the first time in her career, she decided not to follow where the ball was naturally moving. Claire asked herself what kind of life she wanted in 5 years, then worked backward from there. The right move at 25 may be wrong at 35 or 45, and she realized at this juncture she was no longer in proving mode (or what we call “Climber” at Waypoint Works). Another way to put it: what are you prioritizing in your next move?

3. Put money in its place.

It’s important to recognize the role money plays in career decisions, rather than let it be the sole driver. Ask yourself:

• How much money do you need? 
• How much money do you want, and why? What will you do with it? 
• Does your title matter? 
• What satisfaction do you get from status? 
• What no longer serves you? 
• What are your biggest dreams?
• How have your answers to these questions changed over the years? How have you changed? 

If you can be truly honest about your motivations, you'll get closer to the right answers - for you.

4. Build a thesis.

Do not go to your network with: I feel stuck.

There are certain people you can go to with "I feel stuck and have no idea how to move forward," but the majority of your professional network are not those people.  Know your audience.

Claire built a thesis about where her career could go next. It needed to be specific enough to test, and to give people “something to react to”. Let them know how much you value their input, and then outline your thesis. 

Useful thesis language sounds like, “Here’s my understanding of what you do and how you spend your time - is my understanding accurate? Where am I off?” 

When people say “how can I help you,” have a very specific answer ready. Are you asking for advice? An introduction to someone who has a specific role you’re exploring? Honest feedback about your time as colleagues? 

5. Practice on close friends before the big names.

Claire separates the early emotional processing from the later professional asks.

Start with the friends who can wander with you. These are the people who will let you ramble, contradict yourself, and talk in circles while you are still sorting the problem. They are allowed to waste time with you because the relationship is built on high, mutual trust. The relationships you don’t hesitate to think about how you want to use your social capital.

Use that circle to get the mess out (or journal, see a therapist or coach, chat with AI, whatever helps you process best). Avoid tapping your broader professional network during this phase.

6. Test the thesis

By the time you reach out to mentors, former managers, investors, recruiters, or professional contacts, bring them something specific. Continue the data collection. 

Ask for:

• a reaction to your well baked thesis
• a sanity check on your read of the market
• reflections from people who have made a similar move
• And once you’re ready, introductions to the right people
  
  

7. Help them help you

Reduce the work required to help you. This means, pull the relevant hyperlinks, write the template email from them which they can adapt, give them your bio.  Set your own reminders. Follow up. Circle back after you meet the introduction they made, and tell them about the conversation with specifics. Be thorough and thoughtful. Show immense gratitude. Repeat. 

8. You have to be a friend to have a friend

Claire is careful about the relationship currency between professional friends.

You cannot only show up when you need something. You need to make deposits in the relationship over time. The same values that guide friendship are also true for your professional relationships. Remember that you are a representative of the people making introductions for you. Be mindful of who spends time and energy helping you, and plan to return the favor. 

Remember your network is a set of relationships that grow exponentially when they are treated with care.

Compound Interest

It’s more than relationships that can grow through each career season. Claire believes her career change worked because it was not her first experience navigating something difficult and trusting herself through risk.

“The pattern of taking risk and seeing something through, it’s like compound interest,” she said. “It builds on itself.”

The first risk teaches you that you can trust yourself. Over time, you collect evidence that you can act, adjust, recover, and choose again.

Claire believes her thesis to shift from HR to Search was the right one. Executive search uses many of the parts of work that energize her: meeting founders, understanding what they need, solving company-building problems, and helping leaders assemble the teams around them. She also went in with clear eyes about the parts that would be harder.

Her longer-term vision is centered around company building. She is working to build the network and gain the experiences needed to operate at any time as an Operator, Advisor or Investor to Founders and companies she believes in.

Her definition of success has changed too. Earlier in her career, success looked more singular. Now it looks more like freedom: the ability to choose where she spends her time, who she backs, and how she uses her energy, skills, and money.

Claire’s life has been shaped by people who saw her clearly at decisive moments: a teacher who saw intent beneath instead of the failure, a scholarship interviewer who saw character before credentials, and leaders who cared enough to tell her the truth.

She has collected those experiences and learnings and turned them into a mode of operation that's powered a successful and fulfilling career (and life!) along the way.

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