Nobody teaches you how to land your next executive role after 15 years at the same company.

You can run a $500 million business and present to the board. Then someone says, “Tell me about yourself,” and 20 years has to fit into two minutes.

Senior leaders get hired on a clear story, not a perfect resume. Start with the value you created, then build your resume and LinkedIn around it. Work your network instead of applying cold. Pick three words people should remember you by. Then walk into the interview as a peer, deciding whether there is a match.

In this solo episode of The 5% Club for Leaders with Shayla King, I walk through the five-step process I teach inside Land the Role. I spent decades on the other side of this process. I decided who got interviewed, who got promoted, and who got the offer. I know what happens after you leave the interview and the door closes.

What You’ll Learn

• The five steps that get senior leaders hired, in the order that works
• How to answer “tell me about yourself” without reciting 20 years of work
• How to reach out to your network without feeling used or using anyone
• Why a long search lowers the bar, and how to stop it
• What staying in the wrong role is costing you

How to Land Your Next Executive Role in 5 Steps

Five steps, in this order: show your value, build your resume and LinkedIn, work your relationships, define your leadership brand, and nail the interview.

Most leaders start at step two. That is why they spend three weeks moving commas around a resume and still hear crickets.

Step 1: Show your value

Start with your stories, not your resume. Before anyone can market you, you need to know the value you created.

I teach the SHOW method. What was the Situation? How did you lead it? What was the Outcome? Why did it matter?

Build your story vault before the interview. The same questions come up 80% of the time. You are choosing the right story, not inventing one on the spot.

I care about what changed because of what you did.

You built a team. Great. What did the team accomplish? You reduced risk. How much was that worth?

Step 2: Resume and LinkedIn

Now build the resume. Not before.

A resume is not a strategy; it’s simply a tool.

After 15 or 20 years inside one company, your language goes internal. Everybody at your company knows what Project Bluebird means. Nobody outside of it does. So we translate.

One of my clients had been with the same company for 17 years. She did not need me to manufacture impressive experience. She needed help communicating the experience she already had.

She landed an external role and negotiated the offer before our coaching was even finished. That’s the goal.

Your LinkedIn supports the same story. Simplify it. Finish it. Go find the opportunity.

Step 3: Relationships

This is where senior leaders have a huge advantage and often miss it.

When a client tells me she doesn’t really have a network, I ask how long she’s been working. Twenty-three years? You have a network. You just haven’t been treating it like one.

Do not spend six months behind your computer applying to jobs alone. A warm introduction to a hiring manager beats one more LinkedIn or Indeed application.

Be direct. Small talk about someone’s move to Austin, followed by a favor, feels used. Say what you’re looking for. Ask what you can do for them. Remember you would take their call too.

A client had been trying to get promoted to GM for three years. He was already great at his job. We didn’t add one more project. We built a relationship and visibility strategy. Who needed to understand what he was capable of? Which conversations had not happened yet?

He got the promotion in about 90 days, with a $35,000 increase in base pay.

Same guy, same work, better strategy.

Step 4: Your leadership brand

Three words. That’s it.

Interviewers might see eight candidates in a week. When they regroup and someone asks, “What did you think of her?” the answer should be instant. She’s incredibly strategic. She simplifies complex problems. She’s commercially sharp, and people trust her.

Not a paragraph you memorize. Not 17 adjectives. Your stories, resume, LinkedIn, and networking conversations all reinforce the same three words.

Step 5: Nail the interview

You’re not bad at interviewing. You’re rusty.

You lead a thousand people and handle hundred-million-dollar problems without blinking. Then “tell me about yourself” makes you forget your own name. That is rust, and preparation fixes it.

Your SHOW stories will cover most of what they ask. Your three words give you something to reinforce. Now walk in like a peer.

You’re not asking, “Will you please choose me?” You’re asking, “Is there a match here?”

Answer the question and stop talking. Clear, confident, concise. Then pause.

Why Does an Executive Job Search Wear You Down?

Because the process beats you up a little at a time. Silence after applications. Three rounds, then the “we’ve decided to move forward with another candidate” email.

At the beginning, you want an incredible next role. Six months later, you just want it to be over. Maybe I’m asking for too much money. Maybe I should go down a level. Maybe I stayed too long.

How lowered expectations change your results

Shayla King teaches this through The Model: your thoughts create your feelings, your feelings drive your actions, and your actions produce your results.

Think “maybe this won’t happen” and you reach out less. You prepare less. You stop going after the big roles. Then you walk into interviews hoping they choose you, instead of deciding whether you choose them.

I call it get energy. You’re trying to get something from them. You over-explain. You start proving instead of leading.

Stop proving. Start positioning.

What to do when the search stalls

Look at the strategy. Does something need to change? Change it. Is the strategy sound and the process just taking time? Keep going.

Three rejections are not a conclusion about your entire career. We don’t lower the bar because we’re tired. That’s the 5% way.

Should You Negotiate an Executive Job Offer?

Yes. Always have the conversation. Whatever number you start with is the base every future increase builds from.

I coach senior leaders who negotiate multi-million-dollar deals at work and then get nervous asking for another $20,000 for themselves. It does not need to be a chess match. Understand the market and the whole package. Know what matters to you. Ask professionally and calmly.

Decide what you want before you search

Don’t do all this work to land something mid. Get clear on what you want professionally, financially, and in your actual life.

Where do you want to live? How much do you want to travel? Do you want hybrid, more autonomy, a direct line to the CEO, exposure to the board?

One of my favorite questions: If I were choosing my job today, is this the job I would choose? If not, what would I choose?

One of my clients increased her pay by $90,000 in her next move, in the same industry, while working fewer hours. She told me, “I actually feel like my peers respect me now.” More money. Better work. Better life.

What Is Staying in the Wrong Role Costing You?

More than you think. We spend a lot of time weighing the risk of moving and almost none weighing the cost of staying.

If you could be earning more somewhere else, staying has a financial cost. If you could be in bigger rooms with exposure to the CEO, staying has a career cost. If you could have flexibility, a better leader, and a culture where you feel respected, staying has a life cost.

Taking the wrong job because you’re tired of looking costs you too. Do not give the next three years of your life to a role you already know is wrong because it said yes first.

There is also an entire version of your life you will never meet if you keep choosing familiar over better.

Start before you need to

Not actively looking yet? Good. That may be the best time to start. The day someone sends you your dream role should not be the day you go looking for your resume.

Reconnect with your network before you need something. Organize your stories before someone asks for one. Figure out what you want before an offer is sitting in front of you.

When you’re ready, now you have options. When you’re desperate, almost anything can start looking good. Ready is powerful.

Key Takeaways

• Start with your value stories, not your resume. The resume is a tool, not the strategy.
• At the executive level, relationships beat applications. Reach out directly and honestly.
• Three words make you memorable. Use them everywhere.
• Walk into every interview as a peer asking, “Is there a match here?”
• Negotiate every offer, and never lower the bar because the process wore you down.

Frequently Asked Questions

How do I answer “tell me about yourself” as an executive?

Choose the stories that prove your value before the interview, and lead with what changed because of your work. Keep it to a clear two minutes built around your three-word leadership brand. Then stop talking.

How do I network for an executive job without feeling awkward?

Be direct about what you’re looking for instead of burying the ask under small talk. Ask what you can do for them too. People want to help, the same way you would take their call.

Should I negotiate an executive job offer?

Yes. Your starting number is the base for every future increase, so the conversation is always worth having. Understand the market and the full package, know what matters to you, and ask calmly.

Is it worth leaving a company after 15 years?

If you’ve outgrown it, staying has a financial, career, and life cost. Long tenure is not a weakness. The work is translating your internal experience into language the outside market understands.

About Shayla King

Shayla King is a former Chief People Officer and M&A executive and the founder of Evolve Coaching. She spent decades deciding who got interviewed, promoted, and hired, and now coaches Director, VP, and C-suite leaders to win their performance, promotions, pay, and happiness. She hosts The 5% Club for Leaders and holds a Brown University Coaching Certification. Learn more at shaylaking.com.

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