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Three Critical Conversations for Leaders Right Now

Questions that Reconvene People, Realign Teams, and Move Leaders Toward Their New Future


Organizations are facing new and different questions. Some are determining what the future of work looks like in a competitive environment that is shifting around them. Some are on the front lines and have experimented and innovated in short time frames to bring new products or services to bear. And some are just trying to find a viable path forward.

Particularly in times of change, “learning organizations” create space for conversations around these types of challenges. They take a candid look at the current climate in their companies. While recognizing that people experience change in dramatically different ways, they work intentionally to create alignment and harmony. They also take care to define a clear picture of the desired future they are seeking to achieve – providing people a chance to see themselves in it.

This three-card series focuses on our current climate. It provides questions and context that allows for some self-facilitated group conversation. It can take place in a few minutes over a cup of coffee or a few hours in a virtual happy hour. It can work for a small group trying to lead a community organization or an executive team trying to compete in a disrupted environment.

Part 1 is all about what’s really going on for people, teams, and organizations during times of change, transition, and transformation. Part 2 is focused on “Bringing People Back” and figuring out what we can learn from this experience. Part 3 turns toward the path forward while getting clear on priorities, relationships, and a new normal.

Part 1: Acknowledging What We're Going Through

acknowledging How We're Impacted and How We Can Best Lead in This Moment

This first conversation is really about checking in on where people are right now, in the moment. Every individual will be affected very differently – some have direct impacts to families or friends; some have been nose-to-the-grindstone while responding to a long list of urgencies; and some are just trying to stay above water amidst a lot of uncertainty.

There’s no need to solve. No need to react. At its best, it gives people a chance to express themselves, listen to each other, and learn.

While this type of conversation is helpful as a first step in the process, these questions are great to continue to ask. Over the coming months there will be a lot of firsts, a lot of fits and starts, and a lot of new decision points. Some people will be ready to get back to action, while others will be wrestling with what change means to them on any given day. The process for many won’t necessarily be linear. Consistent pulse-checking will help to keep teams and organizations moving.

Part 2: Bringing People Back

Bringing People Back, realigning as a Group, and Capturing Some Key Learnings

The second set of questions adds some purpose and intention to how we best reacclimate. Some people are eagerly reconnecting to their work while others are cautiously finding their footing. There have been moments where people came together to get some great work done – and did it in ways that might transform our businesses in the short and long term. What are the best practices we want to carry forward and some not-so-best practices we want to leave behind?

Acknowledge pride points. Call attention to successes. Get crisp with the opportunities and realizations. Chances are there is plenty that is ripe for a revisit or a refresh. This conversation is all about taking stock of where we are and making the most out of all that’s been learned from this time.

Part 3: Getting Back on Track

Focusing on the Path Forward and the New Realities Teams Might Be Facing

The third and final in this three-card series gets at the most critical conversations leaders should be having today. These questions have you consider what has stayed the same, what’s different, and what needs to be realigned now.

At the beginning of this time, it looked like we might just be pushing the pause button – and in weeks or months, we’d just resume with the priorities and initiatives we charted out for the rest of the year. For some of our work that might still make sense, but for a lot of organizations, those priorities may be altered significantly.

People will look to leaders to reset this compass. Take the time to have the right conversations to get realigned and as clear as possible on a new heading, what the right running rules need to be, and what success should start looking like and feeling like.

The role of leaders

While much of what we’re faced with might be similar, every organization will have its own unique challenges to hurdle. One constant, however, will be the role leaders need to play. The decision points might not always be clear, but there are a few principles that we believe in during times of change.

  • Bring People Together. To think, to talk, and to get reset.

  • Listen with Intention. Hear what people are really saying and listen for the things they can’t quite put words to yet.

  • Provide Information. As much as you can, as often as you can, and as clearly as you can.

  • Find Ways to Help. Sometimes the best thing we can do is just make it a little easier for someone to do what they do best.

  • Lead. People look to you for it.


This series of cards was intended to help leaders navigate the various conversations of the day. For a .pdf version of this set, just e-mail and we’ll be happy to send one your way.

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