The First 90 Days Listening Tour
Listen to customers and employees before changing priorities.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 96%
A new leader spends the first 90 days systematically learning before materially changing priorities. The process begins with immediate outreach to the most important customers, expands into conversations across the broader customer base, and runs alongside an internal tour of employees, structures, capabilities, and cultural strengths. The leader looks for repeated evidence about service gaps, organizational opportunities, and practices worth preserving. Only after this discovery period does the leader adjust priorities. The mechanism reduces assumption-driven decisions, establishes trust during an uncertain transition, and grounds strategic changes in the lived experience of customers and employees rather than the incoming executive's previous playbook.
Origin
Natalie Wolfson described using this approach after becoming Orion's CEO and succeeding company founder Eric Clark. Extracted from Masters in Business.
Core principles
- 01Listen before prescribing change.
- 02Learn the organization from both customer and employee perspectives.
- 03Contact important stakeholders immediately.
- 04Use collected evidence to reprioritize rather than redesign reflexively.
- 05Preserve proven strengths while addressing specific gaps.
How to run it
- 1
Reach Key Customers Immediately
Contact the organization's most important customers on the first day. Explain that hearing their experience is an early leadership priority.
Pro tip Use direct executive outreach rather than delegating the first contact.
Watch out Do not treat conversations with only the largest customers as representative of the entire market.
- 2
Broaden Customer Discovery
Spend the remainder of the listening period speaking with as many customers as practical. Capture recurring needs, frustrations, and valued capabilities.
Pro tip Ask consistent questions so patterns can be compared across conversations.
Watch out Avoid promising solutions before themes have been validated.
- 3
Run an Internal Listening Tour
Meet employees across roles and learn the organizational structure, top performers, working practices, and sources of pride. Ask explicitly about opportunities for improvement.
Pro tip Include frontline employees who experience customer and operational problems directly.
Watch out Do not rely solely on the existing executive team's interpretation of the organization.
- 4
Identify Repeated Signals
Compare customer feedback with internal observations and distinguish isolated requests from systemic issues. Note which existing strengths should remain intact.
Pro tip Prioritize themes supported by both external and internal evidence.
Watch out A visible complaint is not necessarily the highest-impact problem.
- 5
Adjust Priorities Selectively
After the listening period, make focused changes that address validated gaps while preserving the organization's core purpose and strengths.
Pro tip Explain how each new priority connects to what stakeholders said.
Watch out Avoid using the transition as justification for unnecessary wholesale reinvention.
In the wild
After joining Orion, Wolfson contacted the company's top twenty clients on her first day, continued meeting customers for 90 days, and simultaneously learned the team, structure, and employee experience. She then placed more emphasis on scalable client service, flexible integration, and accessible data while retaining Orion's established purpose.
→ A targeted strategic adjustment grounded in stakeholder feedback rather than a disruptive replacement of the founder's vision.
Common mistakes
Arriving With a Finished Plan
Importing a strategy from a previous company can cause the leader to solve assumed problems while overlooking the new organization's actual strengths and constraints.
Listening Only to Senior Leaders
Executive perspectives alone can conceal frontline service problems, cultural realities, and operational bottlenecks.
Changing Everything After the Tour
The purpose of discovery is selective reprioritization, not using stakeholder feedback to rationalize wholesale disruption.
Is it for you?
Best for
New executives taking responsibility for an established organization, especially after a long-tenured or founding leader.
Not ideal for
Immediate crises where legal, financial, security, or safety risks require action before a full listening period can be completed.
From the transcript
“In the first ninety days, I absolutely did a listening tour.”
“In fact, in my very first day, I talked to our top twenty clients, reached out to them, wanted to let them know that I…”
“I also want an internal listening tour. Wanted to get to know the team.”
From the episode
Behavioral Finance and Leadership with Natalie Wolfsen from Orion