Oliver learns that empathy is a method for uncovering the fears, concerns, and risks that prevent organizations from moving forward.
Customer Journey Series: Oliver
This article is part of a customer journey series following “Oliver,” a CTO in a pharma company scaling up to begin commercialization for a new drug. Oliver was facing a growing team, fast growing IT expansion, and collaboration across a rapidly expanding organization.
Each post explores a real coaching conversation or leadership challenge from that journey.
This is the second post in Oliver’s series.
Oliver understood that empathy was going to be an important strategy for his team. So, in his next team meeting, Oliver shared the story of empathizing with his daughters.
To his surprise, his team already understood empathy. They were a team of eight, all of them very bright and mostly Gen Z’ers. They had grown up in schools where empathy was expected and emphasized.
So, the challenge wasn’t empathy.
The challenge was figuring out how to use empathy to help an entire organization plan for an uncertain future.
Scaling Trust When Nothing Feels Safe
The team was responsible for planning and executing an IT strategy for the next 18 months, but the company’s future technology needs were unpredictable.
“In the other departments, people are risk averse, so they don’t like planning ahead,” Oliver explained. “That’s not going to work here. These are million-dollar implementations that can take six months or more. It’s not easy, and it’s not always fast at enterprise scale. Somehow, we have to get ahead of their needs.”
This was not going to be easy. Because of intense regulatory scrutiny, everyone was wary of getting something wrong.
Together Oliver and his team decided not to have a large, company-wide IT meeting. People would feel too exposed.
Instead, they decided to break the planning down department by department and have smaller, one-on-one meetings.
They met one-on-one with leaders and key technical personnel and just told them they wanted to listen to the departments’ vision for technology and how they wanted to use it.
They took their time in meetings, listening and never interrupting as they encountered the uncertainty that comes with forecasting.
Above all, the team was to prioritize making others feel safe.
After the first round, the team assigned to the clinical team said they needed more time to analyze their needs.
The team assigned to the HR team said they need more analysis.
The legal team said they needed time to review.
Oliver and the team discussed what they were hearing. They suspected these were delay tactics and that something else was going on.
Oliver and his team thought people were focusing on operational problems like time, processes, or information because they wanted to externalize the problem. They were trying to make it look like the problem was somewhere else and that they were too busy.
Oliver and I discussed it in coaching. He suspected that under the external problem, there were internal problems—personal fears and concerns that were holding these teams back from being able to act and plan.
I suspected the same. Underneath the delay tactics, there was likely a fear, concern, or desire that was influencing people’s behavior.
“The way to uncover it is to guess what they might be feeling and see how they respond. If you guess right, they will probably confirm it. If you guess wrong, they will probably correct you. This is a classic validation technique.”
We made a list of what might be hiding underneath these operational problems.
- Fear of getting blamed if something goes wrong
- Fear of losing credibility
- Fear of losing control
Instead of focusing on the stated concern, Oliver’s team started focusing on what was hiding beneath it.
Uncovering the Real Concerns
They went for another round of listening. This time, the teams were to try to guess what the fear was driving the delay, saying something like, “I wonder if you’re hesitating because you’re afraid you’ll lose control of your data.”
This worked. In fact, when they suggested that the legal team was delaying because they didn’t want to get blamed if something went wrong, one of the team members looked at them with a wry smile and said, “Now you’re getting smart.”
They kept going back every two weeks. Usually, in the meeting after they guessed what was underneath their delays, they started to open up more and talk about what they were afraid of or what could go wrong.
That’s exactly what Oliver had wanted. He knew that if he could just get them to open up about the risks, they could use technology to mitigate them.
The team discussed the process:
- When people feel heard, they lower their defenses.
- When defenses drop, trust begins to grow.
- When people trust you, they’ll tell you what they’re really worried about.
- And once those concerns become visible, you can solve the real problem instead of the presented one.
It all started with trust. Without trust, organizations get stuck.
The IT Team’s Process
Now they had a process to build enough trust to get people to open up about the risks. They were able to implement it across the company.
They weren’t trying to convince people. They were trying to understand them.
And once people felt heard, they opened up about where the real risks were.
Every department had to trust that the IT department would:
Respect their control over their expertise
Help them find the vulnerabilities and needs
Create enough flexibility to handle any eventuality.
They let them talk about their needs. They listened and recorded the potential problems and the potential breakthroughs.
Then together, they developed a flow chart for information and a business decision tree to make sure everyone knew who was in charge and who was making the decisions.
Once they knew where information needed to flow, and who was responsible for decisions, Oliver’s team was able to start helping others plan IT needs better and get ahead of needs.
It took a couple months, a lot of listening and reassurance, but they started making progress. Planning started going more smoothly and they encountered less resistance.
Over the next few months, they listened, built trust, offered flow charts and decision trees, and collaborated. The team began to respond.
The goal was never to convince people to adopt IT solutions. The goal was to understand what was preventing them from moving forward.
When the IT team understood their real needs—for control, to avoid blame, and to look competent—it was much easier to collaborate on the risk factors.
People started opening up about where the risks were. That’s where Oliver’s team could help them.
Looking back, Oliver realized they had stumbled onto a repeatable leadership system:
- Listen
- Make people feel heard
- Build trust
- Uncover concerns
- Reveal the real problem
- Collaborate
- Build solutions
Continue the Journey
← Previous Post | Next Post →
Keep Learning
Return to Customer Journeys Hub
Explore the Leadership Framework
