A dare that could transform an arms-length relationship

by | May 4, 2026 | Monthly-ish tips

This post is part of our Monthly-ish Tips series.

Two things converged for me recently. I’ve been working on my new book manuscript that includes a never-told short story about an unusual exchange with a client procurement manager. Then just a few days ago a workshop participant wanted to explore the challenges of working with a client’s procurement office. So I’m taking this synchronicity as a sign to share some ideas more widely. 

The book is based on the Get Real manifesto, and the new short story is in the chapter called “Being vulnerable takes chutzpah.” It’s about the opposite of conventional wisdom that says, “never let them see you sweat” and the power of choosing to disclose something you could easily avoid.  

I’ve written about disclosures before, which are a kind of confession—not the criminal or religious kind, but the kind that better your relationships as a result. Disclosures can improve any relationship, but especially those that are typically constrained or strained, as is often the case with the procurement-vendor dynamic. 

While my own track record is mixed, I get better at seizing these paradoxical opportunities as time passes and experience proves the benefits again and again.  

Here’s the draft story: 

I was working with a procurement leader for a large client organization—someone I’d never met or actually spoken to. The relationship was courteous but formal and procedural, as is so often the case with contracting. I was supposed to review a final agreement draft and send back any changes. What should have taken me a couple of days stretched into weeks. When I finally sent the file, my baser instincts tempted me to lead with a vague apology for my delay. Instead, I did the opposite and said: “I have no good excuse, other than I dreaded the tedium of making sure I was sending you back a document in its near-final state. In reality, it took embarrassingly little time for me to do that once I got over my mental hurdle.”  

I got two immediate replies: Within thirty minutes the VP business sponsor on cc replied only to me, saying “I love your honesty and humanity. Just saying. Thanks for practicing what you preach.” And within two hours the procurement leader replied to all, first quoting my words back to me verbatim then adding, “I empathize with you so deeply, sometimes our biggest obstacles are the ones we imagine for ourselves.”  

Now, I ask you: when was the last time a procurement person deeply empathized with you? I’ve had my own share of arms-length exchanges with contracts reps and I bet you have too. This wasn’t one of them. 

I actually have a handful of ideas for how to improve your relationship with procurement staff (a bookmark for an upcoming post, maybe). But for now, I simply invite you to consider what’s possible when you step outside the norm and dare to reveal rather than conceal—especially in a work relationship traditionally marked by distance and formality. 

Make It Real 

Carpe diem. Notice the next time you’re tempted to conceal not reveal and do the opposite of what your baser instincts suggest.  

I double dog dare you … 

 

 

 

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Andrea Howe

As the founder of The Get Real Project, I am the steward of our vision and our service offerings, as well as a workshop leader and keynote speaker. Above all else, I am an entrepreneur on a mission: to kick conventional business wisdom to the curb and transform how people work together as a result. I am also the co-author, with Charles H. Green, of The Trusted Advisor Fieldbook (Wiley, 2012).

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