Issue #107

How to Rip an Incumbent Out by the Roots

Every seller runs into the same brick wall: the incumbent.

They know the people, the process, and they probably wrote half the spec. for the tender.

To beat them, you can’t play inside their frame. You have to surface what’s hidden, widen the conversation, and make the buyer see things the incumbent hoped would stay invisible.

The Five Advantages of the Incumbent and How to Break Them

1. They Know the System

The incumbent helped shape the tender. They know which boxes to tick and which buzzwords unlock approval.

Counter: Don’t let the tender be your only source of truth. Run your own discovery with ops, finance, compliance, and end-users.

Ask what’s missing, what frustrates them, and what never makes it onto paper. Weave those insights into your bid. That shows you’re not just filling in forms, you’re solving the real problems.

​Click here to see how to get information without seeming to ask questions, very useful when talking to the incumbent and their coach.

2. They’ve Spread into the Cracks

Over time, incumbents bolt on ad-hoc fixes, free reports, and favours that aren’t in the contract but keep them sticky.

Counter: Name the cracks. Ask, “What do they do for you that isn’t written into the agreement?” Buyers usually pause, then admit a list.

That’s when you show the cost, the risk, or how you’d cover it more cleanly. What looked like loyalty now looks like scope creep.

3. They Feel Safe

I once heard an ops director in a bid review say, “If we stick with them, nobody gets fired.” That’s the incumbent’s shield.

Counter: Show that “safe” is just stuck. Highlight the risks of standing still: creeping costs, supplier fatigue, missed innovation.

Then structure your offer with off-ramps, phased rollout, trial periods, opt-out clauses. You’re not asking the buyer to gamble. You’re giving them insurance.

4. They Own the Relationships

Years of meetings, favours, and golf days mean they feel part of the furniture.

Counter: Build authority, not familiarity. Bring heavyweight references, regulatory endorsements or executive sponsors.

The buyer might like the incumbent, but the board will side with the choice they can defend.

5. They Know Buyer Laziness

They’ve worked out which reports get read and which dashboards rot in SharePoint. They cater to the path of least resistance.

Counter: Out-simplify them. Deliver draft board slides, one-page impact statements, and cost-benefit models.

If your bid makes decision-makers look sharper with less effort, the incumbent’s comfort makes them look unprofessional.

The Five Advantages of the Challenger and How to Defend Them

1. Fresh Thinking

You’re not weighed down by legacy systems and outdated processes. You can introduce cleaner designs and sharper ideas.

​Click here for a reminder about how to think about your value to the prospect.

Incumbent defence: They’re untested here.

Your play: Show evidence of these ideas already working in similar or tougher environments.

2. Speed to Benefit

New suppliers can implement with fewer moving parts, so results can arrive faster. The incumbent will be trying to defend their margin, not improve the operation.

Incumbent defence: They don’t understand our complexity, speed means shortcuts.

Your play: Provide examples of fast but controlled rollouts. Back them with credible timelines and reference clients who saw early gains.
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3. Attention from the Top

As a new win, the account will matter. Senior people will be visible, available and accountable.

Incumbent defence: We give you senior access too.

Your play: Demonstrate it. Bring senior leaders into the pitch, name executive sponsors, and commit to regular oversight meetings.

Get them to tell a convincing story about how life will be with your solution, click here for a reminder how to do that.​

4. Fit to Business Reality

You can design around the client’s current needs instead of forcing the solution into legacy processes.

Incumbent defence: They don’t understand the complexity, tailoring will drag on.

Your play: Show real cases where you integrated with messy systems, mirrored client reporting or customised without endless delay. Fit isn’t a promise, it’s a proven track record.

5. Cost Transparency

You start clean. No bolt-ons, no hidden extras.

Incumbent defence: We give you extras for free.

Your play: Put those freebies under the light. Show they are hidden costs the client pays elsewhere. Position your pricing as predictable and fair.

The Elephant in the Room: The Cost of Change

The biggest obstacle to change is rarely loyalty. It’s the disruption cost; retraining, dual-running, integration headaches, and political fallout if it stumbles. The incumbent doesn’t need to mention it, everyone feels it.

Incumbent line: Why spend extra? You already know we work.

Your play: Call it out before they do. Admit transition has a price, then contain it: time-limited, fully supported, no hidden extras and clear ROI.

Position it as an unavoidable investment that only grows worse if delayed. Buyers respect challengers who acknowledge the pain and show how to manage it.

The Point

Incumbents win through inertia. They wrote the rules and grew roots in the cracks.

But challengers have tools too, fresh ideas, faster benefits, real senior attention, tighter fit to business reality, cleaner pricing, and the courage to face the cost of change head-on.

WYAD

When you’re up against the old guard, don’t play by their rules.

Run your own discovery, expose the hidden extras, confront the cost of change, and hammer home the strengths only a challenger can bring.

That’s how you prise them out.

Here's a short video about how to shape comparisons, so you don't get tricked by the incumbent into using their numbers and definitions - use your own.

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If you want to get your team trained up in the basics of enterprise sales click here.

My course is a full suite of punchy, 5 to 10 minute videos like this one.

You can integrate them into your team meetings to coach your team to excellence, step by step..

And you can always email me if you want to discuss coaching or consultancy for you or your team.