The legal team was very risk averse and getting in the way of progress. Oliver uses trust to promote cross-functional collaboration.


Oliver, a CTO seeking to be more than a tech guy and become a strategic partner.

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 fourth post in Oliver’s series.


As Oliver’s influence grew and people trusted his strategic partnership, Oliver stopped trying to win one-on-one arguments and instead built organizational alignment around the larger mission.

After the first IT council, Oliver’s team identified 44 large IT systems they needed to complete to serve all the teams’ needs. It was a massive job, and they were given resources to hire an implementation contractor to help.

But now he was running into a new roadblock. The legal team was very risk averse and getting in the way of progress.

Last year, when commercialization looked good, the executive team had brought in a new General Counsel who oversaw the legal team and every process had started to slow down.

“She spends 6 months negotiating small risk items in a contract, but the benefits she is negotiating are items that are unlikely to happen. We can’t afford the 6-month delay in implementation.”

Oliver observed that she took it as a point of pride to get a small concession out of Google or other big IT companies.

But he was frustrated. “These are million-dollar implementations. No one else negotiates these things. We are stressed and this is causing unnecessary delays that hold up whole teams. Now we are getting blamed.”

The Difficult Conversations Approach

The first thing Oliver tried was to have a difficult conversation and see if he could make some progress. His goal was to listen and understand her problems. He would be careful to avoid judgment, just try to discuss the problem while demonstrating respect for her. If he was successful, he would get her to empathize with how the delays were affecting his team and the whole company. 

He planned to open with a vision of what he was trying to do. “The goal is to protect the launch and do our best for the company. This is not about you or us. We are on the same team.”

Then he would try to raise her awareness of the cost and risks of delays.

His main point was to convey that the quality of the vendor and its system mattered.

“When we choose vendors, we have a choice. The vendors who are more willing to negotiate are weaker vendors, so there is more risk of failure to the company. The stronger vendors are less willing to negotiate, but they are better systems and ultimately are more likely to protect the company.”

He would also point out that implementing a system takes three to six months. “If legal delays by 6 months negotiating the contract, the departments don’t get the data systems for a year or more. They need them sooner as commercialization is happening quickly. What are they to do if they don’t have the systems they need when we commercialize?”

Then he would ask her, how can you help us get better vendors more quickly?

In theory, this was a good approach, but unfortunately here, it didn’t work. She refused to budge. She took no responsibility for delays and tried to convince Oliver that this was normal.

This was not Oliver’s first commercialization process, and he knew it was not normal. Oliver had been empathetic and respectful. But empathy alone doesn’t always work.

So, he tried another tactic.

Using Peers to Make Your Case

Oliver started with pre-meetings, quietly discussing the problem with other company leaders and found that the legal team was creating the same delays for other teams as well.

He decided to use the IT Council to see if he could make some progress.

He knew he had credibility when he raised alarm bells, so he announced the next IT Council theme as Mitigating Risks.

There were about 20 leaders in the room. Oliver practiced his meeting deck with me and got a few comments before the big meeting.

He would set it up like this:

He started with the mission of the IT council: to discuss the problems they were having and see if technology could make fixes easier and more consistent. “Individuals should not be put in a position of taking risks.”

He went on: “The purpose of technology is to find standardized and safe solutions to the risks people faced in their daily work. Whether that was standardizing financial statements to reduce human errors, or standardizing clinical data to improve accurate record keeping for regulators and doctors as proof began to roll in. They should be able to rely on processes that enable safe, accurate reporting so the company relies on the data, whether it’s financial or clinical.”

He saw this as a cross-functional task force on readiness for the next phase when the drug goes on the market, and manufacturing, sales, and marketing all ramp up.

Today’s goal was to identify risk gaps so they could be addressed.

Because he had done pre-meetings and helped leaders find ways to safely identify and talk about the risks they were facing, he knew that other leaders were having problems with the delays from the legal department too.

One by one, department leaders discussed the risks their teams were dealing with. More than half of them mentioned delays by legal as the legal team as a major source of delay and risk for their team.

At the end of the meeting, the head of the legal department had heard the complaints. The CEO was there and everyone was looking at her.

“We have to re-think some things,” is all she said.

After the meeting, Oliver debriefed the meeting in coaching. “The IT council is functioning exactly as I hoped it would. It’s a place where we can surface risk factors together, without blame or shame, and just solve them.”

Oliver noted that when he first raised the concern, it was easy for her to dismiss it as his opinion. But when leaders from across the company described the same problem, it became clear that something needed to change.

And then Oliver discussed what he was learning.

“I understand her position. When I was solving everyone’s problems, I felt useful and that I was adding something. But now I see that leadership is more powerful when it empowers other people, and is less focused on heroics.”

Oliver’s self-awareness and understanding of leadership had deepened.

Over the course of the next couple of months, the legal team stopped seeking small wins in contracts through repeated delays, and actually started to approve better contracts with better vendors in reasonable times.

By the time the next IT council came around three months later, many leaders praised legal for helping them accomplish their goals. Everyone came out happy.

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