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The Toughest Lessons I’ve Ever Learned: 6 Powerful Leaders Share Their Stories

From saying no to Steve Jobs to losing Adidas, these successful CEOs share what they lost--and gained--from difficult decisions.


by Marla Tabaka

Have you ever made a difficult, even poor, choice and learned nothing from it? Here's why it's important to find the nuggets of wisdom in even the poorest of decisions.

James Green, CEO of Magnetic

1. Even if your boss is Steve Jobs, it's okay to say no.

The most difficult learning experience I've ever worked through was saying no to one of the most persuasive people I've ever met--Steve Jobs. Steve offered me a position that I felt was not suited to me, and after taking a deep breath, I told him no. I learned that even when you have the opportunity to put that big name company on your resume, or work for someone so brilliant, if it's not a good fit you need to stick to your values and decline. Consequently, when I was the one in a position of leadership, I understood that you must pay incredible attention to what someone wants to do when you hire them. If what they want isn't exactly what the company needs, you shouldn't hire them, no matter how smart, driven, or successful they are. Steve ended up offering me another position more in line with my interests and expertise, and I got the chance to work with a company that allowed me to grow exponentially in my career.

Claire Telling, Joint-CEO, Grace Blue

2. Address red flags immediately.

One of the hardest lessons I have learned, is to act quickly to address talent performance issues. There's a great adage: be slow to hire and quick to fire. One time I did the reverse--I hired on a hunch and got excited by the wrong things about this person and didn't look closely enough at whether he could do the job. I didn't do this person justice by not agreeing to part ways sooner. It is much easier to ignore a situation where a team member is not the right cultural fit or is not pulling their weight. If left unaddressed, the wrong person can drag down a culture and a business in a matter of months, which can be impossibly hard to bounce back from. The minute you sense a red flag with one of your staff, act on it right away. Be swift to identify talent problems, and be quick, yet thoughtful, to make decisions. It will keep positive momentum high, and eliminate the need for more costly action later.

Justin Tobin, Founder and CEO of DDG

3. Test Small, Fail Fast.

The hardest lesson I've learned is that you can't afford to overestimate a client's appetite for transformation. I work with leaders of Fortune 500

companies, many of them legacy corporations grappling with making changes to their internal processes and mindsets to keep up with increasing competition from more nimble startups. Early on, I once pushed a client to make too many changes at once, they recoiled, and we ultimately disengaged. While they may have sold me on their eagerness to transform their business, I realized that part of my job needs to be to accurately assess their appetite for the speed of that transformation to better set expectations for both the client and my team. As a result, I've adopted the following mantra that is now core to my professional and personal approach to life: test small, fail fast and fail often. If your test cases are small, your failures will be small and your lessons frequent.

Stephen Beck, Co-Founder & CEO of Engine Digital

4. Don't be above asking for help when you need it.

As an agency hired for our thinking, knowledge, and craft, I often assume we're best suited to solve almost any business problem. But solving your own internal problems introduces a completely different kind of challenge. For the first time in our 14-year history, we sought the expertise of a consultancy to help us correct a broken part of our engagement model. Without a doubt this was worth the cost and time. We were able to create clarity, empower our team, and eliminate gaps that lead to unknowns, risks, and frustrations. Like most businesses, we were too close to the problem to define a solution, regardless of its obvious simplicity. I learned that reaching out and seeking help can be an enlightening experience, shining new light on my role as a business leader.

Guy Hayward, Global CEO at KBS

5. Evolve or Lose Business (I did).

I was one of the founders of a creative agency in Amsterdam, and our first client was Adidas. We were able to win the business off the back of our true passion for sports and our prior experience in the field. But over time, our client's priorities changed, and they wanted to focus more on the fashion side of the business. Instead of evolving with them and moving our business in parallel to the direction they were going, we sat around talking (and praying) for them to go back. Instead of rebuilding our team to deliver great fashion work, we hankered after the 'good old days'. Our client ended up parting ways with us, and the agency is still feeling ripple effects from the departure. Now that I've moved on and am leading a global company, I've realized that in business, and in all aspects of life, I have to remain open to the fact that priorities around me will always shift. The only way to inspire impactful change is to look inward. Personal change is the only way I can move the needle for my clients, my business, and myself.

Andrew Bennett, Global CEO, Havas Creative Group

6. Look beyond what is "perfect on paper".

When I first was in a position to hire people, I'm not sure I realized just how vital it is to pay attention to personality and cultural fit. We've all come across candidates who are perfect on paper and hit just the right marks in terms of skills, education, experience, and interests. But some simply don't know, or learn, how to work in a way that has a positive influence on a team. It can be tempting to hire someone who comes across as a superstar, but I learned quickly that no amount of talent is sufficient to offset an outsized ego, negative attitude, or lack of consideration toward others. My advice: Never hire anyone you wouldn't be happy to spend long hours with under the most trying of circumstances.

Inc.