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Lessons Learned

How To Coach Confidence In People Who Are Feeling Defeated

The self-doubt that follows a setback can be turned into a useful tool for doing better. Here's how to activate it.

How To Coach Confidence In People Who Are Feeling Defeated

Supporters of Democratic presidential nominee former Secretary of State Hillary Clinton as they watch the results roll in from the states on election night at the Javits Center November 8, 2016.

[Photo: Matt McClain /The Washington Post via Getty Images]

Around half the population of the United States woke up on Wednesday morning to enormous disappointment. In a stunning upset, Donald Trump defeated Hillary Clinton in the race for president, leaving Trump supporters elated and many Clinton backers devastated.

But in my work as a coach, I've found that even the most crushing defeats can ultimately be channeled into energy for forging ahead. Regaining confidence is an uphill battle, and it takes a crowd—or at least two people, talking things out—to pull an someone out of a funk. Here's how it can be done.

Setbacks Cast Long Shadows

During my first coaching with a client called Molly, I asked what salary she’d like from a company where she was interviewing for a competitive position. Her reply sounded familiar.

"Wait a sec," I asked. "What’s your current salary?"

Molly shrugged. "It’s the same. I know—You expect me to ask for more. But after what happened, I don’t think I’m worth even that."

Molly was a senior-level copywriter. She was well-liked at her current job at a prestigious brand where her skills had helped the company succeed. Nevertheless, she’d been outmaneuvered for a promotion. Molly was so crushed that all she could do was keep plugging away at her work. But her heart wasn’t in it anymore.

Six months after the demotion (that’s how she thought of it, anyway), Molly came to me for coaching. As someone who helps creative professionals negotiate during some of the toughest times in their careers, I had no trouble recognizing her sense of defeat. An acquaintance of Molly’s asked her if she’d like to interview for a position to lead a team at his company, which was a similarly prestigious brand. "Perfect," Molly thought. "I love their brand and they do really courageous work. I’m going for it!" Problem solved, she thought.

But then the fears set in. New opportunities after a setback don’t always erase the feelings that the setback instills. That self-doubt lingers, and it can sabotage even the most promising of steps forward. Here’s what I’ve learned it takes to reignite someone’s self-confidence after hitting a low point.

What A Coach’s Job Consists Of

In my experience, self-doubt, and its cousin, anxiety, can actually compel us to make our work better. But before we can get motivated (or re-motivated), we first need to feel confident. And that’s something anybody can help do for someone who’s feeling down. To take on those coaching duties yourself, here’s what to do.

Meet them where they are. Listen before you challenge assumptions. The worries might sound silly, but they’re quite real to the worrier.

Be specific in your feedback. Empty praise will either boost someone only temporarily, or it’ll come off sounding as hollow as it is and crush your credibility. Give details and keep it real.

Use their own words to vanquish self-doubt. Getting them to simply describe their accomplishments, as well as their doubts, can help offer some perspective. Sometimes people just need a chance to become a little more self-critical, then that sense of defeat can begin to dissolve.

Pull the camera back—way, way back. Again, your job as a coach and confidence-booster is to offer the widest perspective. A radically different perspective can bring radical results. Anytime you see a way to reframe someone’s point of view, offer an alternative take.

Getting From Self-Doubt To A New Direction

In our first meeting, Molly described the new position before launching into all the reasons she wasn’t right for it:

"I wasn’t good enough at my current job. That’s why they didn’t promote me."

"The new company will know I got passed over."

"My work isn’t relevant. The companies are in totally different verticals."

"I’m not confident enough."

I let her vent, then asked the salary question and heard her uncertainty again.

"Molly, this is your career," I told her. "My job is to support you getting the job you want, the way you want it."

Now I needed to help her chip away at her doubts, born of her latest setback—which first meant getting away from it. "Tell me about your most successful campaigns to date," I told her. "Give me the details on strategy and how your messaging supported the company’s goals."

Talking about her achievements carried us well into our next coaching session. I could see Molly’s confidence rising as she talked through the impact of her work. "Molly, it’s clear your work expresses the company’s culture and sells product. That’s powerful," I remarked.

In our third and final session, I needed Molly to broaden her view of her op-tions and get more narrowly specific about her salary ask. I started by summarizing her key accomplishments. Then I fired off an out-of-the-blue question.

"So, Molly, let’s take a look at some alternatives. What about taking another shot at your current company? You’ve created powerful work there and we both know they’ve noticed."

It was clear as Molly sat back that the idea of a new job had been her entire focus. She hadn’t thought about how to make things work without jumping ship.

"Well," she laughed, "I’ve been so down on my writing that I’m trying to learn new skills. Social media strategy has been really engaging and my current employer is way behind. There might be something in that." I just let that idea hang in the air before resuming our conversation.

"Tell me, Molly, now that you’ve had time to reflect, what salary are you going to ask for in the interview?"

She mentioned a number 30% higher than her previous notion. "I’ve done some research and asked around," she said. "Given what I can do for them and my accomplishments, that salary seems fair." Molly’s new view of her accomplishments had given her the self-efficacy she needed to repack her thinking with a realistic view of what she could offer.

But although a new job was the catalyst for that change, it didn’t have to be the outcome. Before her interview, Molly asked her current boss if he’d be interested in her assessment of where they could take their social media strategy. His positive response furthered her confidence. She hit the interview poised and ready, but when the offer came a week later, she turned it down: Her current boss created a new position heading up social media, and she took that instead.


Ted Leonhardt is a designer and illustrator, and former global creative director of FITCH Worldwide. His specialized approach to negotiation helps creative workers build on their strengths and own their value in the marketplace. Follow Ted on Twitter at @tedleonhardt.

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