Unanswerable Human Questions

In an ordinary work day, most of my clients are either the founders or leaders of high-growth tech startups. Some lead whole companies—but many lead either a sales function or a technology function. They may be CROs, CTOs, Engineering Leads or VP of Sales. But they all have something in common. Each of their organizations contends with tension between their sales and their technology teams. They also have tension between Marketing and Sales, between Cistomer Success and Product and so on!

Depending on which function the client leads, they have a compelling story about their counterpart; a story that explains some deficit in their own performance.

Sales leaders (and this includes Founders) often feel that engineering is too slow in delivering new features. Or, they believe that the default response to all requests for product modifications is a resounding “NO!”.

Technology leaders have the inverse complaint. ‘Instead of selling what we have, they say yes to every fantasy their prospect describes.” Then they ask the engineering team to fulfill that request—with NO understanding of what it would take or how much the team is already doing.

Both functions feel like it should be obvious that they are the lynchpin! Sales says that without them, there’s no revenue. So there.

But engineering (or AI or manufacturing) say that they are the verybsource of the product. No product, no sales. no sales, no business. QED!

Tech feels misunderstood and underappreciated.

Sales feels misunderstood and under-appreciated.

Symbiosis

When we step back and look at the whole picture, it’s plain that both teams are integral to any functioning technology company. Tech is right: “No product, No Business”; as is sales: “No Revenue, No Business.” So how can these two essential teams, and most importantly, their leaders, thrive instead of struggling?

A Child’s Lingering Insecurity

There are a lot of different ways to approach the situation. And I have written about them many times. But one thing that occurs to me every time I hear a complaint of this nature is that there is a huge gap of understanding and empathy; plus, a lack of appreciation and acknowledgement. On both sides!

Why does each of these teams feel that it is so important to stress how essential their function is? Why don’t the leaders of these team take for granted that EVERYONE knows they are critical?

Everyone agrees with BOTH arguments: Without revenue, there is no business. And, without the product there is no business. No one would dispute those facts—and yet those leaders feel like no one fully understand them. Why?

The Long Shadow of Childhood

This isn’t really that different than an individual claiming that they are not appreciated in a marriage, or a person on the team wondering is their boss approves of their work.

At an individual level, each of us goes through life with doubt. Those doubts stem from decisions and perceptions that we had when we were children; often when we were so young that we couldn’t put things into words and certainly not into perspective. So, we invented explanations for those moments that seemed inexplicable.

Maybe we felt overlooked, couldn’t get Dad’s attention, were scolded for something a sibling did, made a mistake and mistook correction for an attack. Nothing about that is unusual. A child perceives a parent’s momentary distraction as disinterest, or can’t grasp a concept at school and surmises that they are stupid—rather than that they just haven’t figured it out yet.

The view of the world from the perspective of a small child is distorted. And in the millions of moments, interactions, observations and experiences that comprise our childhoods, we misapprehend things as being personal that are not.

We start our lives as scientists, and as part of that natural process of explaining the world, we develop theories about ourselves, our abilities, and the nature of other people. Each of us comes up with a unique mental model. And many aspects of those models include areas where we mistakenly drew the conclusion that we were less smart, appreciated, likable, visible or adept.

For the rest of our lives, we try to compensate for one of those arbitrary moments. Because we are adults, and we are committed professionals, we largely disguise those feelings. We act confident. We act humble. We act congenial. But, beneath that, we have questions about our role, our ability, our value, and our status. So, we express those questions through office dynamics and politics.

The Unanswerable

None of those childhood decisions have anything to do with technology or sales. Nor do they have anything to do with business or organizations.

They have to do with our common humanity that is with us in every moment of life. And if we know that that hidden dynamic is part and parcel of engaging with human beings, especially in collaborative and cooperative settings, then maybe as leaders we should allow for it.

There are overriding themes. Most of us—at least those who are not psychopaths—experience life through the filters of the fears, insecurities and shame we crafted in childhood. They live as questions we wanted answered definitively from someone other than a colleague or boss. We wanted assurance from Mom that we were good. We needed guarantees from Dad that he would always love us. We craved the approval of a fellow classmate in grade school—or relief from shame that we felt over a one-time mistake.

Since those questions, needs and desires belonged to our childhood selves, and those selves no longer exist, nothing ever fulfills them. Your mother’s assurance to you now, or the school friends’ social inclusion next month does nothing for the childhood feeling of shame, loss, insecurity or longing. They are “unanswerable” questions.

Empathy and Appreciation

As leaders, we have an opportunity to build organizations that provide a steady stream of appreciation and acknowledgment. Part of the benefit of doing so is to help our employees (and ourselves) reduce the volume of their own unanswerable questions. When appreciation, acknowledgement and compassion are missing, people’s innate self-doubt and sense of being unappreciated become louder. We find ways to get noticed, or we become discontent, bored and start looking for a new job.

So it is in our interest as leaders to cultivate appreciation, empathy, compassion and acknowledgement.

We can start by helping our team members develop empathy for every other member of the larger team.

One way to do that is to cross train.

The Sales Experience

There is no amount of explanation that any sales person could give an engineer that would truly describe the sense of the precariousness that one feels one trying to close the deal. Selling is scary. The possibility of failing to close the deal is terrifying. And in the midst of that process, a sales person feels a great deal of pressure. Plus, in most organizations, sales people MUST close deals to get commissions. They have their livelihood partially at stake.

While all that is going on, she must appear relaxed, confident, and to keep her attention in the world of the prospect rather than on her own concerns.

If engineers had a visceral sense of that experience, it would better enable them to cooperate with their sales peers, and to help figure out how to fulfill what is needed to close a deal.

Racing the Roadmap Clock

For engineers, they are the silent engine behind the organization’s product. And most every day, and every week, the team is furiously working to hit deadlines so that investors, customers, the Board of Directors, and the founder are satisfied.

Moreover, engineers are often tasked with solving problems that have not been solved before. So it is, though they are in the world champion Rubik’s Cube contest, racing the clock to solve the puzzle. And at the same time, as they are focused on achieving a single piece of this puzzle, they are being interrupted with requests to solve trivial problems, build new things because the sales person just sold it, and fix bugs that threaten the security or stability of the product. The pressure is immense.

How could a sales person gain a deep appreciation of how it really is for an engineer, or for the leader of an engineering team?

Cross-Train, Shadow, Share

One possible way to build real appreciation and empathy is to have people shadow others in the organization. That would look like a sales rep working with the engineering team for a day or two. Actually being in the meetings, in the stand-up, and looking over the shoulder of an engineer at work. It would not be exciting work. But, it would engender a sense of the pressure and intensity of what it’s like to be an engineer.

It is easier to have an engineer shadow a sales person. Because the work of selling, while skilled, is familiar activity. All of us have conversations, make phone calls and send emails. An engineer joining the sales team, for a few days would begin to understand how challenging the conversations are when a prospect is dragging their feet. They would hear the musings of a prospect over a function they imagine with solve their problem, and understand the pressure that the sales person feels to accede to that request.

Cross training every individual in an organization by having them shadow, or actually join a team in a contrasting function, makes sense. Although it would cost temporally in productivity, it pays dividends in appreciation, empathy, and cohesion.

Sales people that have worked on engineering teams understand what they are promising, and the stress that it will add to the engineering team if they do so. They think more carefully about those choices.

Engineers who spend time on sales teens, learn to appreciate how hard it is to close a deal, and why a sales person might be forced to sell something speculative. They can advocate for their sales peers, and collaborate with them in providing what is needed to close the deal.

This kind of cross training is less about being able to do another person‘s job than it is about learning to appreciate, acknowledge, and empathize with another person’s experience. When your organization has a scaffold of this kind of empathy, there is far less rivalry between functions. Cohesion goes up. And people who work in the organization have a sense that their peers are striving to answer their unanswerable questions—even if it isn’t possible. Each of us thrives when we feel understood and valued.

Are you a leader of a technology team? Building the skills of leadership and negotiation is different than the skills you learned to be an engineer or technologist. The Leaders Lab Mastermind is a program for people like you! If you want to become a world-class leader, learn more here, or schedule a chat with me.

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