I’ve sat through hundreds of deal reviews and loss reviews in my sales career. And if I’m honest, many of them were deeply flawed and a complete waste of time. Not because the people were bad, but because the environment was wrong.

In too many sales organisations, deal reviews feel less like collaborative forums and more like hostile inspections of rep performance. I know this because I once accidentally created exactly that environment myself - without even realising it!

A Lesson I Learned the Hard Way at HubSpot

When I joined HubSpot, one of the first things I asked for simply (or so I thought) was:

“Let’s schedule Deal Reviews for the top deals across JAPAC in the coming quarter.”

What followed was completely unexpected. A quiet panic quickly rippled across the sales organisation. Reps started whispering:

• “Why is the JAPAC GM inspecting my deal?”

• “Am I in trouble?”

• “What have I done wrong on this opportunity?”

That reaction was my wake-up call. What I intended as a collaborative leadership exercise was being interpreted as inspection - not support, not learning, not value-add.

And the reps weren’t wrong. At that point, that’s exactly how it looked! I realised quickly that if I didn’t change the framing (and the environment) fast, these sessions would destroy trust and deliver zero insight.

What Changed Everything

So I made the shift explicit. These sessions were not inspections. Instead, they were collaborative problem solving forums.

I was clear that:

• No one was “in trouble”. - this was not a "witch hunt"

• The sole purpose was to help the rep win the deal

• The CRM was the source of truth. Nothing else was required to be prepared

• My role was to support and facilitate, not judge

• The team was there to help solution, not be passive

And then I went a step further. I didn’t just ask questions - I took ownership.

Ownership for:

• Specific actions that moved the deal forward

• Executive relationships to multi-thread within the account

• Strategic outreach to engage directly with key decision makers

• Removing obstacles the rep couldn’t move alone

And that mattered more than any words I could have said.

When the Culture Fully Turned

Word spread quickly. The narrative shifted from:

“The new GM is inspecting deals” to “The new GM actually helps you close deals.”

Within a few short months:

• Reps stopped dreading deal reviews

• They started requesting them of me

• Deals surfaced earlier in the cycle

• Risks were shared openly and discussed as a team

Then something really interesting happened. Reps began reaching out proactively. Not because they were told to - but because they saw the value.

I started getting messages on Slack like:

“Can we do a quick deal huddle to brainstorm how we overcome this obstacle together?”

That’s when I knew the environment had fundamentally changed. Deal reviews had stopped being a test - and became a tool that added tremendous value to the rep's success.

What This Taught Me About Psychological Safety

Here’s the lesson that I was trying to role model:

Psychological safety isn’t declared - it’s demonstrated.

Reps don’t believe words. They believe behaviour. When leaders:

• Share ownership for the outcome

• Contribute real value to their deal

• Use authority to unblock, not interrogate

• And genuinely care about the rep’s success

Safety follows. And once safety exists, insight flows freely and quickly.

Why Most Deal Reviews Still Fail

Most deal reviews fail not because reps are defensive or leaders lack intent. They fail because:

• The environment feels hostile

• Authority dominates curiosity

• Learning is secondary to optics

Here's the reality - you simply cannot demand honesty from a room that feels unsafe.

What High-Quality Deal Reviews Actually Look Like

In healthy sales cultures:

• No bespoke decks are required - CRM is the only source of truth

• Leaders facilitate, not dominate

• Teams brainstorm gaps and obstacles together

• Actions are clear, owned, and tracked

• Learning feeds directly into future deals

A Challenge for Sales Leaders

If your deal reviews feel tense, defensive, or performative, ask yourself:

• Do reps see these sessions as inspections - or a source of support?

• Do I contribute value beyond questions and inspection?

• Am I willing to share ownership of the outcome?

• Would reps request this session if it were optional?

If not, this isn’t a rep issue. It’s a leadership design issue. Because when reps start asking for deal reviews, you’ve stopped inspecting and started leading.

At Growth Getters, I help sales leaders redesign the moments that matter:

• Deal reviews

• Loss reviews

• Pipeline councils

• Forecast calls

Not to make them softer - but to make them actually useful. If your deal reviews create anxiety instead of insight, it’s time to change the environment, not demand more preparation or action.

Feel free to reach out directly at dan@growthgetters.com.au for an initial confidential discussion.