Difficult Decisions and Challenging Conversations—The Stuff of Leadership (and Organization) Success

The road to a difficult decision is paved with one or more challenging conversations.

The two—difficult decisions and challenging conversations—are inextricably linked. Effective leaders and high performing teams work hard to develop skills and conventions for navigating challenging conversations in pursuit of hard decisions surrounding strategy, investment, structure, and talent.

For too many others, however, difficult decisions languish, and challenging conversations are something to be avoided to keep things collegial.

Culture Check on Challenging Conversations:

One of the key factors I look for when advising management teams on strategy and change is their ability to talk effectively about the tough topics.

High performing teams and cultures adopt a clinical approach and use deliberate discussion and decision-making tools to surface the right issues, shoot down biases, and uncover the relevant or missing facts. The discussions are often intense and even passionate, but never personal. It’s clear the individuals involved understand the power of the group in seeking the right choice.

It’s not surprising in organizations where top management is practiced at conducting challenging conversations in pursuit of difficult decisions, the same behaviors are visible in the broader culture.

Sadly, a majority of environments I encounter struggle with both conversations and decisions. From the overly collegial to individuals in open warfare versus each other, there’s no discipline or commitment to effective discussion and decision-making processes.

It’s no surprise in these settings the broader culture tends to reflect top management’s dysfunctional behaviors.

Strengthening Your Challenging Conversations and Difficult Decisions Approaches:

Comfort with challenging conversations is developed through practice around a structured process. The same goes for making difficult decisions. Unfortunately, b-school education and corporate training often fall short in these areas.

In a perfect world, all of us are steeped in the latest and greatest insights surrounding how the brain works and how humans are motivated. Lacking advanced degrees in neuroscience, behavioral psychology, and communication theory, we’re left to our designs, often to the disadvantage of our organizations and teams.

However, a few simple but not simplistic adjustments to our approaches can help us begin the process of strengthening our discussion and decision-making muscles.

8 Ideas to Help Your Challenging Conversations and Difficult Decisions:

Use these ideas to get started strengthening your organization’s or team’s effectiveness in navigating tough topics.

1. Start with the values.

Amplify the importance and accountability for challenging conversations in pursuit of difficult decisions as a core value in the culture. Teams and leaders that get this right are open about the importance and obligation of every person to confidently engage in these discussions in pursuit of performance. Call it out!

2. Stop discussion swirl.

Adopt a specific facilitation process for tough topics. I love Edward De Bono’s parallel thinking/parallel dialog process outlined in his classic, Six Thinking Hats. I long ago adapted his approach to fit my style; however, the theory remains the same: stop the swirl by getting the group to focus on one narrow theme at a time. (See my article: Better Design for Workplace Discussions)

3. Always link to the business issues.

Teach the group to describe issues with a direct link to the business. Much of our time in meetings is spent debating variations of, “What I think is… .” Instead, hold people accountable to, “This approach will impact our business by… .” While it can still be gamed, my experience is requiring people to think about the business connection strengthens the quality of the idea discussion. We then focus on the issue and the impact on the business and not John’s or Mary’s opinion.

4. Use framing to improve decision options.

Spend a great deal of time developing two or more frames for the issue and then developing alternative solutions. In simple terms, reframe a perceived problem as an opportunity and develop a unique solution to exploit the opportunity. You are drawing upon the reality that humans produce different responses to threats versus opportunities. As a manager, I want to look at both sides of this issue. (See my article: How to Frame Your Decisions for Success.)

5. Ask these two critical questions about the facts.

Drawing on the parallel dialog technique above, ask the ever-important and mostly missing questions:

  • What do we know? (What facts do we have?)
  • What do we need to know (What facts do we need to find?)

It’s the latter that is mostly missing and this tactic works

6. Start every decision-discussion with this key question:

Start every decision-making discussion with the question: “How are we going to make this decision?” Just the act of agreeing on structure for a decision-making process improves the probability of reaching a decision.

7. Create a coach-advocate, not a devil’s advocate.

I find the devil’s advocate role to offer as many minuses as plusses and much prefer creating a coaching role to support discussion and decision-making processes. While creating this role may require investment in training, ultimately having a capable, confident individual assessing discussion and decision-processes and surfacing assumptions is well worth the investment.

8. Keep score.

The goal is continuous improvement, not instant mastery. Document all critical decisions and the surrounding context and identify expectations. Return over time to review actual outcomes and identify potential areas of weakness in the process. Incorporate the positive and constructive lessons into the process moving forward.

The Bottom-Line for Now:

To strengthen decision-making effectiveness, you must enhance discussion quality. The two are inextricably linked. Effective leaders teach their teams how to talk and how to decide. Remember, the road to success is paved with difficult decisions and challenging conversations.

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About the Author:

Art Petty is a coach, speaker and workshop presenter focusing on helping professionals and organizations learn to survive and thrive in an era of change. When he is not speaking, Art serves senior executives, business owners and high potential professionals as a coach and strategy advisor. Additionally, Art’s books are widely used in leadership development programs. To learn more or discuss a challenge, contact Art.

One Comment

  1. Greg Robinson June 26, 2018 at 9:37 pm - Reply

    This is a great post Art. As I read your article, it occurred to me that what you’ve outlined is a method for building trust. Teams lacking trust usually suffer from the problems you describe where they either avoid conflict altogether or difficult discussions tend to devolve into personal attacks. These 8 ideas are all important in building a culture of trust, which is at the heart of any high performing team. Thanks for the insight.

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