Phase 3: Leadership & Team Assessment
The leadership team is the lever. If it doesn't work, nothing else will.
The technology leadership team is the lever through which everything else happens. If this team functions well — if they trust each other, debate honestly, commit to decisions, hold each other accountable, and focus on collective results — problems get surfaced early, decisions get made cleanly, and execution follows.
If the leadership team doesn't function, no amount of process improvement, reorganization, or technology investment will compensate.
The Five Dysfunctions lens
This assessment draws on Patrick Lencioni's Five Dysfunctions model, adapted for technology leadership:
Absence of Trust — Team members are unwilling to be vulnerable, admit mistakes, or ask for help.
Fear of Conflict — Artificial harmony prevents honest debate. People agree in the meeting and disagree in the hallway.
Lack of Commitment — Without real debate, decisions don't get genuine buy-in. Ambiguity becomes a hiding place.
Avoidance of Accountability — Low performers are tolerated. Missed commitments go unaddressed.
Inattention to Results — Individual goals take precedence over team outcomes.
The Primary Team Question
One of the most diagnostic questions: "Who do you consider your primary team — this leadership team, or your direct reports?"
If every leader answers "my direct reports," you have a collection of silos, not a leadership team.
Three layers of assessment
Leadership Team — Directors and above. Five Dysfunctions lens, strategic alignment, cross-functional dynamics.
Managers — Team leads. How leadership decisions translate into daily reality.
Individual Contributors — The ground truth. Tool quality, deployment confidence, psychological safety.
The patterns across these three layers are revelatory. When leadership says "we have high trust" and ICs describe hiding mistakes — that's a finding.
The Primary Team Question
"Who do you consider your primary team — this leadership team, or your direct reports?" If every leader answers "my direct reports," you have a collection of silos, not a team.
What you hear — and what it means
Leadership team interviews focus on dynamics, trust, decision-making, and strategic alignment.
“We agree in the meeting and then everyone goes back and does what they were going to do anyway.”
VP Engineering“I'd rather not bring up problems in the leadership meeting. It never goes well.”
Director of PlatformWhat Leadership feedback tells you
If leaders avoid conflict and don't commit genuinely, the organization below them will optimize locally rather than globally. The Silo Republic is almost always downstream of leadership team dysfunction.
Sample questions for this phase
Leadership
How would you describe the trust level within this leadership team?
When there's a disagreement, how does this team resolve it?
Who do you consider your primary team?
Managers
How clearly are strategic priorities communicated to your team?
When priorities shift, how do you find out?
What does your team need that they're not getting from leadership?
Individual Contributors
When something goes wrong in production, what happens?
How confident are you in the deployment process?
Do you feel safe raising concerns or disagreeing with your manager?
The complete question set covers additional questions across multiple topics for each stakeholder group. Available in the TRUST Toolkit.