The Hardest Thing You Need To Be Doing

The Hardest Thing You Need To Be Doing

A few weeks ago, I facilitated a conversation between the CEO and the CTO of a tech company. The CEO, like many tech founders, is also the Head of Product. He’s a visionary for more, better, faster. He is always pushing. The CTO, on the other hand, knows what goes into each iteration and wants to protect his team. He often finds himself pushing back.

Both wanted to know how they could minimize the tension between them.

And you know what? I fell for it.

I focused our conversations on how to smooth things over. I won’t say that it was wrong, but I missed a far greater opportunity – to grow their tolerance for discomfort. We all know the virtues of constructive conflict. It sparks innovation, increased commitment and accountability, and leads to stronger relationships. And yet, I chose to focus my attention on how to ease the tension rather than how to use the tension.

Why? Probably for the same reason that all of you choose not to avoid or minimize conflict. Because it’s messy. It takes too much time. It’s uncomfortable. And there are no guarantees.

Yet something the CTO wrote me has continued to stick with me. Prior to our meeting, I emailed the two executives questions to prepare, one of which was: Imagine that you two were really leveraging your differences and there was flow in the relationship, what would be different?  

The CTO, using the metaphor of swimming, sent a thoughtful response that maybe flow wasn’t actually possible:

“I wonder though, is flow possible when we’re talking about tough issues? Where we’re slightly in conflict? I’m not sure ‘flow’ applies. I can enter a state of flow when swimming and the sea is like a millpond. Perfectly clear, no waves, no surf, no chop, no currents. Just stroke after stroke after stroke, exactly the same, for hours and my brain can tune out. But swimming in choppy conditions is a fight. There’s no state of flow, no relaxation. Every stroke is a fight; to control the catch, to sight where I’m going, to breathe without being slapped by a wave. It’s just pure aggression (and I hate it). Flow is easy when the going is easy; is it even possible when the waves get up?”

His metaphor challenged the notion that flow was the aim. Perhaps we shouldn’t be pretending that choppy conditions are anything but hard, frustrating and exhausting. But it also drove home the point that not only is conflict unavoidable, it is the only way to get stronger individually, as a team and as an organization.

Constructive conflict is a necessity for any organization that seeks to be extraordinary.

Constructive conflict is a necessity for any organization that seeks to be extraordinary. 


Since then, I’ve been thinking more about this metaphor of swimming in rough, choppy seas. The CTO happens to face the cold inhospitable waves of the Atlantic, so I tried to imagine why someone would choose to do something so hard. What was the point of it? Then I remembered years ago when I went got certified to scuba dive. At the time, I was living in San Francisco. After completing the pool work, you had the option of doing your open water certification in Monterey Bay. Most people opted for the warm waters of Hawaii. I decided on Monterey.

I was exhausted before I ever put my fin in the water. I pulled on 2 thick wetsuits, a hood, gloves, not to mention the extra weight on my belt to counter the buoyancy of the wetsuits. As I waded into the dark, cold waters filled with kelp, my breathing was shallow, and I could feel panic building. More than once, I almost backed out.

No, flow wasn’t possible for me that day. And that wasn’t the point. It was to push me to my edge. To pretend that it was anything other than hard would have been careless. But it made me a better diver – stronger, more prepared and less likely to panic. Not unlike what the right kind of conflict can do.

Conflict and tension happen every day in every organization. One side wants to speed things up. The other side wants to slow things down.

And while it often feels personal and like something to fix, the tension exists for a reason. Just like checks and balances in the American political system, functional roles are often designed to be at odds with each other. They create a natural push and pull to ensure that change happens incrementally and that no single person or functional area can unwittingly put the organization at risk.

Just like checks and balances in the American political system, functional roles are often designed to be at odds with each other. They create a natural push and pull.


So how do you foster meaningful conflict?

  1. Acknowledge that this kind of conflict is not just inevitable, but necessary.  Rather than trying to deny it, avoid it or mask it, consider that conflict can seed creativity. No one wants to hurt someone’s feelings, undermine them or make someone uncomfortable. So instead they minimize it.  Postpone it. Say yes when they mean no. It’s uncomfortable. It takes more time. It may lead to sleepless nights. But it results in better ideas. 

  2. In the Five Dysfunctions of a Team, Patrick Lencioni points out that true commitment cannot happen if there is not conflict. If your organization is struggling with accountability, could it be that keeping the peace is leading to false agreement? Check out the model here.

  3. Depersonalize it. Constructive conflict is rooted in the issue. Destructive conflict is personal. Try seeing that this is the person’s job rather than attributing it to their personality. 

  4. Align on outcomes and find areas of agreement. When both parties are focused on the same end goal, it builds trust.

  5. Minimize misunderstanding by having actual conversations. Written conversations are counter-productive when there is an underlying emotional tone. Talk don’t write. If you insist on writing, then be sure to follow it up with a real conversation. 

  6. Learn to speak each other’s language. There is a reason why personality assessments are widely used. We all gravitate to roles that reflect how we think and communicate. Those communication styles may often be vastly different from the other person. By learning to bridge the communication gap, it can keep the focus on the issue rather than on personality. 

Starla Sireno specializes in Executive Communication Skills Coaching in NYC. Whether it is an individual conversation or a group facilitation, Starla has an unparalleled ability to create deeply meaningful, useful and practical learning experiences for her clients. Inquire how you can work with Starla or her team.

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