Win Without Pitching®: Thinking

Share on twitter
Share on facebook
Share on linkedin

Confidence is not evenly distributed in the world. I recognize that I probably have more than is merited, but I’ve been at the other end of the spectrum, too, having once worked for someone who seemed to actively undermine the confidence of her subordinates as a means of building her own. I quickly discovered that in the wrong environment it doesn’t take long for your confidence to crash to zero, even when starting with more than your deserved share.

Strategic Coach founder Dan Sullivan says that the most valuable asset of an entrepreneurial organization is the confidence of the entrepreneur. When I first heard those words I instantly knew them to be true. More than that, however, hearing the words spoken out loud gave me permission to talk to others—my team and my business partner wife—about the issues. I confessed all the things I did (some of which caused me slight embarrassment) to build and maintain my confidence, like getting my shoes shined (even when they don’t need it), buying a new shirt (I’ve got lots), giving money away (hard to explain this one but it’s about recentering my perspective), or delaying or completely ignoring tasks I’m not great at. And this is just the beginning of my long list. I won’t share the truly weird stuff.

I explained that I wasn’t crazy, shallow or irresponsible. I simply knew the value—to me and the company—of my confidence and I did whatever I felt was necessary to keep it high at the times I needed it most. My wife responded with 100% support and no longer questions my absurd and sometimes extravagant rituals. I feel like I’m out of the closet, finally sharing a deep secret. I’ve been met with understanding when I was worried I would be ridiculed (and have my confidence eroded!)

Entrepreneurs need confidence because, at the highest level, their job is to place bets on the future. The risks inherent in those bets are the source of the firm’s profit. An entrepreneur with low confidence is someone who quits making bets and for whom the label “self-employed” would be more accurate than “entrepreneur.” The self-employed create jobs for themselves (and perhaps a few others) with no real profit beyond their wage. The difference between self-employment and entrepreneurship is simply the confidence to bet on change.

Business Development People Need Confidence, Too

Entrepreneurs aren’t the only ones who need confidence to succeed. For people in sales, business development and other roles on the front lines with clients and prospects, the need to build and protect confidence is equally paramount.

You need the confidence to stop talking. To put away the PowerPoint deck. To be comfortable with silence. To raise your prices. To push back on flawed or onerous selection processes. To politely but firmly challenge any of the client’s assumptions. To push back on your boss who wants you to call the prospect again when the right move is to let them breathe. To do the right thing for the client even when the firm is trying to meet payroll. To take more risk in the engagement as a means of alleviating some of the client’s risk and getting the deal done.

You need confidence to deftly swat away inappropriate requests for another time-wasting meeting, or a lengthy unpaid proposal. You need confidence to face down a surly procurement person and their bag of unsavory tricks.

We teach a lot of contrarian things in the Win Without Pitching program, and the people most likely to succeed at these alternative approaches are simply the ones that are able to summon the confidence to try something new, even when it’s contrary to how they’ve always done it.

On the balance sheet of your career, confidence is your number one asset. It is even more valuable than your reputation.

If you want to ensure you head into the coming year with you and your key people operating at high confidence, simply begin with an open conversation in which you acknowledge that confidence is an invaluable asset. Talk about the things you do to maintain your confidence and then ask each other, what do you need from me to help boost your confidence?


Blair Enns
Blair Enns is the Win Without Pitching founder and CEO and the author of The Win Without Pitching Manifesto and Pricing Creativity: A Guide to Profit Beyond the Billable Hour.
We help agencies close more business the Win Without Pitching Way

You will get a curated collection of Blair’s best writing, videos, and podcast episodes immediately after signing up.

Then, you’ll receive Blair’s latest work as it’s published.

Sign up to get our best advice delivered straight to your inbox

Recent Thinking

Getting Paid

There are three keys to getting paid: start with new standards for new clients, summon the resolve to enforce your new standards the moment client behavior starts to slip, and be willing to walk away from clients that don’t honor their commitments.

The Five Levels of Pricing Success

In this post I lay out the five levels of pricing success and ask you to do an assessment of where you are now. Then I identify the best resources to help you move up from your current level.