Can This Deal Be Saved? The Art of Asking “What Matters?”
Denise Logan

Last week I was talking with a banker about how to save a deal of his that was spiraling out of control. It seemed the Seller had become less and less responsive over the past several weeks and then, suddenly, threw up a wacky deal term out of nowhere that threatened to kill the deal. The entire deal team was left scrambling wondering, “Where the heck did that curve ball come from?”

He had sought me out to see if I had any ideas about how we could get his deal back on track, as one of the attorneys involved had brought me in on a prior deal and told him I was “A CEO Whisperer.”

I asked the banker a single question… “What Matters?”


At the same conference where I spoke with this banker, I had the privilege of spending time with some first time attendees. I offered to each of them that they could use me as “home base” during the conference. I told them, “Any time you feel out of sorts or don’t know how to begin a conversation with someone new, come join whichever conversation I am engaged in and I will readily introduce you to the person I am talking to. You’ll meet some interesting people.”

One of these new people said to me later, “Denise, you rarely start a conversation with a question about what that person’s job is or what their company does. Why?”

To me, that’s inconsequential small talk that doesn’t matter. People get bored with repeating news, sports and weather – or its business version … “What do you do? What does your company do?” They’ve already answered those questions several hundred times during the conference before they meet me. You can tell by the way their voice falls flat and their eyes glaze as they give their standardized elevator pitch.

You might be saying to yourself, “But that’s what we do at conferences, we try to learn about each other’s business. It’s business development that takes us to conferences, after all, Denise! I can’t afford to spend time talking to every person who’s there.”

I’m going to challenge you on that before we return to my conversation with the banker. How much do you actually learn about the other person or their company with that standardized line of questions about “what they do”? And, how long do you stay involved in a conversation with that person once you satisfy your ulterior, yet unspoken, question “Can I make any money from this conversation with you?”

One of the newbies at the conference said to me, “These firms all sound the same to me. It’s hard for me to really suss out how they’re different from each other.” I just grinned. He was like the child who said “The Emperor has no clothes!” He had revealed a truth that few wish to acknowledge. Most of our businesses are not really that different from our competitors.

The reality is that most of us are more inclined to do business with people we trust, with those with whom we have relationships and with whom our “what matters” aligns.

Through our carefull (it’s not a typo, I meant filled with care; not walled off, exploitive and deceptive) conversations, we have an opportunity to learn what matters to each other and discern with whom we will enjoy doing business.

I think I’m lucky that my business name opens the door to a deeper conversation. Nearly every time someone looked at my name tag, they would repeat back to me, “Chase What Matters. Huh, what matters?”

I live for those moments. The ones where we’re going to drop down a layer into something richer. It’s those conversations that are going to become doorways to relationships. Relationships are what drive our businesses. Without them, they are simply mechanical transactions, devoid of the essence of What Matters to either party. It leaves us stuck in roles, unable to bring our unique creativity to the equation of business before us.

If you check in with yourself, you can recall the differences between deals you’ve done when you were in a relationship with the other party and when you were simply a transaction to be done. How did it feel? Whose “what matters” ruled the interaction?

Learning What Matters

What matters to me? You’ve probably guessed, it’s depth. Deep relationships, conversations with substance, genuine connection and meaning. I’m wired for connection and service. But, before I can serve, I need to know what matters… to me and to the person I am about to serve. It’s no different for you and your business.

When I have the opportunity to reflect the question back … “What Matters to YOU?” … I’m often rewarded with a glimpse behind the façade. Often, what I hear is about their humanity and what gets in the way of them living the full life they crave. A deeper, meaning-filled life. The shallow “wants” fall away as we talk about What Matters to them.

That changes the interaction … immediately, we’re dropping into another space together. One filled with import and meaning. I always pause. As if we have our hand on the knob of a door and we are crossing the threshold of a room together, because that pause breaks the momentum of habit. It gives us a choice. That choice, the only choice we really have, is to be open or closed, to the meaning of what matters to each of us in what we are about to embark upon together.

Moments of meaning and depth define us. They shape our choices. They create new opportunities. But we must be open to a different kind of deeper conversation about What Matters as we become the authors of our lives or assist others in their businesses.

Applying What Matters to the Deal

The banker asked me, “Can you get this deal back on track so it will close?” I asked him if that was what mattered … and to whom.

I’m not clueless about the financial implications of having a deal not close. I get it, the entire deal team and all of its players have time, money and resources at stake in getting this thing across the finish line. But force alone isn’t going to make it happen, nor should it.

When I ask What Matters? I want to know many things – whether closing this deal, at all costs, even if it is to the detriment of their client, is what matters to him and the rest of the deal team. I want to know what matters to his client beyond this deal and what is getting in the way of it for him. I want to know where their mutual What Matters align – beyond just the financial elements – and whether we can get them to align in a way that will allow the deal to successfully close or whether everyone’s interests are best served by walking away sooner rather than later, without anyone feeling exploited.

The way we do deals leaves an imprint on us and our deal partners. It’s why understanding what matters (preferably, earlier rather than later) and being open to the deeper, care-filled conversations along the way is better for everyone involved. It leads to less strain, more satisfaction and better subsequent collaborations between deal partners. Facilitating those deeper conversations among deal partners is an art and it comes from a different place than the one we use in purely linear, “just the facts” deal making.

In my experience, this sudden curve ball in a deal typically means that there is an emotional need of the Seller that isn’t getting met. Perhaps he just got scared because he remembered watching his father die shortly after retiring and he can’t imagine what he’s going to do with himself after the sale of the business he’s spent his own life building. Perhaps he just learned that his dream of sailing around the world isn’t going to happen because his wife finally told him she has no interest in traveling away from the grandchildren. Perhaps his best friend told him he should hold out for more money and he’s afraid of looking like a chump.

What we know for certain is that What Matters, what really matters under the sudden curve ball, needs to be addressed. It probably ISN’T about what it looks like it’s about, either. And, the Seller isn’t going to tell it to someone whose What Matters isn’t aligned with theirs. Once I get to be with the Seller, to understand What Matters and we address the underlying emotional needs, then we can ferret out next steps toward resolving the deal.

And, if you don’t know what really matters to you or you don’t care about what really matters to your client, it won’t matter how many of those shallow networking conversations you have at a conference. No matter what your pitch is, eventually, others will recognize that the only thing that matters to you is forcing a solution that satisfies your needs. All that networking and business development will be for naught in the end and you’ll be left with the truth of your life and the way you conducted yourself – as a selfish player who didn’t really care what mattered to anyone else. I know you are better than that at your core.

We’re talking about your business and your life and those of the people who entrust their lives and businesses to you. So, do the work to get clear about what matters and chase that. I can promise you, it really is about more than whether you close this single deal.

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