Leading in Times of Volatility: Questions to Sit With

How curiosity, compassion, and creativity help us lead amidst choppy market conditions.

The challenges and constraints of leading through adverse market conditions can be your headwinds or your tailwinds. Having an opinion about your new constraints/challenges and making a few strong bets can be key. Conservatism with resources often makes us feel safer, but underfunding your best bets due to an unexamined desire for safety, can put the whole enterprise at risk. Ask yourself: where do you have conviction? Where there is conviction, take the risk: fully fund bets that represent good work, done well, for the right reasons.

For moments like these, inquiry can help us understand our own motivations, improve our organizational awareness, and anchor our working relationships in value-seeking priority. These questions have helped my clients, but also helped me and my teams maintain focus during tumultuous times in the past.

The first line of inquiry is internally focused, touching on what transitions you might be facing personally and how you want to be. Many of these lines of inquiry come from Jeff Riddle and Jim Marsden who co-authored this article in 2020 when we were coming to terms with COVID-19.

• How are you?
• What feels like a big struggle now?
• What keeps you up at night?
• Who would you like to choose to be as a leader through this crisis? An understandably stressed and anxious version of you, or a more resourced, confident, and grounded version of yourself?
• Allow yourself to connect with a past challenging time when you and your team were all at their best. A peak experience, that you’re proud of and that you found rewarding:
• What qualities do you notice were present with you as a leader?
• What aspect of yourself would you like to have present with you now?
• What made this past experience rewarding for you?
• How might you bring your insights from the above alive in your current situation?
• What support or help would you ask for? And from whom (leadership team, coach, partner, friend, mentor, etc.)
• What do you want to stand for as a leader?
• Who would you like to choose to be as a company through this crisis?
• What do you want to stand for as a company?

Then, consider these questions at an organization or team level focus.

• What is your top priority? How has this shifted from your priorities a few months ago?
• Where can you narrow your team’s focus? Note: this increases resources to the remaining priorities.
• How can one or two challenges/constraints of the new macro environment serve as the wind at your back?
• How can you align your team to discern the bets you wish to fund more aggressively vs the bets do you wish to pass on?

Inquiry that continually asks us to focus our efforts on the most valuable activities can be shared and repeated (even weekly) in conversations with your leaders and team members to provide support and accountability:

• Are there any commitments, assumptions, or expectations that are limiting our ability to grow the company, knowing what we know now?
• What do we want to change, knowing what we know now?
• (On a scale of 1 to 10) How confident are you that you know how to grow the value of the company with your team? (Follow-up: What would you need in order to be a 10?)
• (On a scale of 1 to 10) How confident are you that the work your team focused on last week was the most important work for you to grow the value of the company? (Follow-up: What would help next week be a 10?)

Inquiry is a powerful tool that can support you at the personal level, the organizational level, and the relationship level. Inquiry doesn’t ask us to be certain, it asks us to be curious, introspective, creative, compassionate, and courageous; it’s these qualities that help us lead amidst choppy market conditions.