EFFECTIVE CHALLENGE

Challenging well is an art. In a society that values reaction over listening, challenging well has never been more vital.

What do you do when you have a gut feeling that something isn’t right, but you don’t know how to fix it? Have you ever been in a situation when you know something is off, but can’t find the best path toward a better solution?

Rather than creating conflict, or avoiding conflict altogether, use the below guide to learn the steps to challenge well. At the end of the day, we’re trying to get the right and best solution. It’s not personal.

EFFECTIVE CHALLENGE STEPS:

hange the mind. Tell yourself it’s right and I have a duty to question it anyway.

ave empathy. What is the other person thinking/feeling/expecting?

lign outcomes. What is our desired future state? What are we trying to do here?

ean into the direction. How does our solution get us to our desired future state?

et go and add one. Let go of the attachment to the solution and add a positive change?

verything goes. How could we approach the solution in a totally different way?

egotiate a pathway. Where do we go from here?

et honest. Was anything left unsaid, and did I share 100% of my truth?

ncourage agreement. How can we agree on the direction together?

Repeat this statement out loud. This solution is the right and best solution to achieve our desired future state.

In this exercise, you will reflect on two unique scenarios and run through the effective challenge framework to help you rethink (a) a past decision and (b) an important future decision. You can run through this exercise individually or share it with your work team/broader organization. The framework is meant to spur debate and discourse, opening people up to the art of challenging.

Scenario A

What is an important decision you recently made?

How did you make that decision?

Go through the Effective Challenge steps for that decision. Write below: hange the mind. It’s right and I have a duty to question it anyway. ave empathy. What is the other person thinking/feeling/expecting? lign outcomes. What is our desired future state? What are we trying to do here? ean into the direction. How does our solution get us to our desired future state? et go and add one. Let go of the attachment to the solution and add a positive change? verything goes. How could we approach the solution in a totally different way? egotiate a pathway. Where do we go from here? et honest. Was anything left unsaid and did I share 100% of my truth? ncourage agreement. How can we agree on the direction together? three steps long:

Repeat this statement out loud. This solution is the right and best solution to achieve our desired future state.

1. Acknowledge that you already have the right solution.

2. Let go and add one: Give up your attachment to the original solution. Then add one new thought, changing or questioning what already exists. The power of simply adding or changing one thing, no matter how small or large, is transformational. This is the most freeing and often most creative step.

3. Encourage agreement: Agree on the one change. What single change takes our original solution to the next level, and how will we revise our original solution so it’s the best solution?

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I embrace the challenge. I apply it in many different settings and find it useful for arriving at both simple solutions and the most complex. Here’s an example. At an eclectic dinner party with a diverse group around the table, including clergy from multiple faiths, we began debating the idea of the challenge. The rabbi talked about the name “Israel” and how it translates to “wrestling with God.” I became fascinated as he explained the name’s meaning and the expectations surrounding it. He talked about the constant struggle of this classic conflict and how important gaining different perspectives is to his depth of faith. He described how two people can walk into a room with two perspectives and leave with three. His point was that challenge is embedded in his and other faiths and is an expected component of discourse on important topics. With that discipline, leaving with an informed, different perspective than where you started is a likely outcome.

This idea of mental sparring is why we have boxing bags and gloves in our Leadership Learning Labs, each adorned with graffiti that says, “Who’s your sparring partner?” We want the challenge to be front and center as we teach leaders how to spar constructively on topics of importance. We teach the skill of challenge and help leaders convert it to an art form. Of course, there is no ring, we are simply teaching the art of the spar and necessity of challenging with our words.

We also use challenge in how we interview. We want people to like us, but we want them to know us from the first encounter. If you cannot withstand the multiple behavioral interviews , you will not excel in our company. We challenge candidates with our probing questions, our expectations, and our redirects and intentional interruptions. We don’t want the practiced you—we want the real you. And we have developed a scientific approach to elicit the information we need. Our interviewees need to understand our culture of challenging everything.

We open workshops with a challenge as well. We ask leaders to fill out five oversized sticky notes by asking five open-ended questions, all starting with the word “why.” It is the only time we accept the word “why” from leadership because, by its nature, it is divisive and confrontational. We ask leaders to challenge themselves and their colleagues with their questions. This is not about confrontation, but true challenge—and it is always done anonymously, to ensure the full impact and truth imbedded in the question. When it comes to the Effective Challenge, the word “why” is a weapon to be used wisely, or never at all.

We also challenge how leaders see their organizations and their own leadership. Remember my earlier axiom that a leader has one choice: change the people or change the people. On the surface these options are the same. But leaders don’t lead on the surface; they go deep. Leaders have the ability to create a framework for others to challenge themselves and create their own change. If they are unable to make the change, then leaders are challenged to change the people—as in, out of the organization. In either case, the challenge lies in the leader’s ability to see the needed change and create the pathway. Sometimes it requires the simple add-one element; other times, a fundamental remake.

Some find my relentless desire to probe exhausting. Perhaps I would have been better off sticking with my law school endeavors. But I am not questioning to fluster; rather, to encourage. At times, the challenge evokes a raw, unvarnished response—sometimes tears or sheer anger. In either case, I am prepared to accept whatever my challenge elicits.

Today’s leader must be armed with the tools that allow them to lead with courage. They must be committed to the truth and be willing to push people right to or just beyond their personal comfort line. We bring people into this state because we believe that they can contribute and create at a different level, even when it feels like the opposite to them. We believe that the brain has a misunderstood capacity and ability to fundamentally explore and push boundaries. Tapping this capacity is why we do what we do and why we expect so much more from our people. We believe they can get to a higher state with more creative output. When we allow the effective challenge to do its best work, reaching that higher state comes naturally.

Leaders Who Challenge

Early in his career, Blair Garrou, co-founder and managing director of Mercury Fund, had become known for successfully replicating the Silicon Valley playbook in Middle American cities by helping to create viable startup technology ecosystems there. Supply and demand had left an imbalance of capital available for funding technology start-ups, and Blair was looking to build the next generation of great deals outside of both Wall Street and Silicon Valley. For over a decade, Mercury focused on the underrepresented entrepreneur, in this case a startup founder without access to capital. However, over time, Blair found that the traditional playbook had left massive demographics behind without access to capital and resources. He wanted to create belonging and access for Black, Hispanic, and female entrepreneurs who previously had been dismissed as “undesired and underserved” for venture capital. Mercury believed that there were incredible investments to be made in these founders, but it would take real inclusive work at both the fund and the community level to execute, so they began to build relationships with organizations who worked with historically underserved startup founders.

Over the next few years, by all measures, the firm was wildly successful. But that didn’t stop the phone call Blair made to Deutser, not only to question but to challenge everything in his business.

The call came on a dreary Sunday afternoon as COVID-19 was challenging many of Mercury’s entrepreneurial companies and bearing down Blair’s spirit. He questioned whether to rebrand the entirety of his company or rethink it altogether. He challenged the future and his ability to more meaningfully serve the communities he so dearly wanted to reach.