Executive Summary
Building buyer trust means being honest about where your service has worked, where it has fallen short and what you have changed as a result. For managed service providers selling to UK businesses, this matters because buyers are weighing up the risk of disruption, wasted investment and choosing the wrong IT partner.
Case studies and testimonials provide useful evidence. But claiming that every project has delivered a perfect result can create doubt. Buyers understand that problems happen. What they want to know is how you respond when they do.
When a buyer asks about a failure, explain what happened, take responsibility for your part, describe the lesson and show the practical changes you made. Then connect those changes to their situation. You do not need to lead every sales conversation with your worst project. You do need to answer difficult questions honestly and give buyers evidence that you have learned.
Why does buyer trust matter in MSP sales
Buyers aren’t stupid.
And yet many sales and business people treat them as if they are.
We talk about our brilliant service. Our experienced team. The customers who love us. We show the testimonials and explain how much better things will be once the buyer starts working with us.
All of that has a place. But while you are describing the positives, the person opposite you is thinking about risk.
Will this actually work for us? What happens if it doesn’t? And will this person still answer the phone when we have a problem?
If you run an MSP, your buyer may be trusting you with the systems their people need to work every day. Choosing you could affect their operations, their customers and their own reputation inside the business.
A confident presentation helps. An honest conversation about those concerns helps them judge whether that confidence is deserved.
What are buyers really asking when they request a case study
“Can you show me examples of where the solution has worked?”
It is a reasonable question. You should be able to provide relevant evidence and explain the circumstances behind the result.
But there is often another question sitting underneath it.
“It worked for them. How do I know it will work for us?”
Your buyer is weighing up the differences. Perhaps the customer in your case study had a dedicated internal IT team. Perhaps their systems were simpler. Perhaps they had more time to prepare or a bigger budget.
They want to believe you, but they are checking whether your example really applies to their business.
This is why a case study needs more than a happy customer quote. Explain what the customer needed, what made the project work and what the customer had to contribute. Help the buyer understand the conditions behind the outcome.
Then give them space to ask the awkward question.
“Where hasn’t it worked?”
Can admitting a failure help you build buyer trust
Yes, it can. But simply admitting that something went wrong is not enough.
Most of us who sell know the skeletons in our own cupboards. The customers where it went to shit. The projects where we had grand plans and the result fell short.
We never wanted it to happen. In many cases, we still feel bad about it. But we cannot erase it.
And guess what? Buyers know that too.
They understand that people leave, expectations become unrealistic and projects run into problems. They do not need you to pretend that every seed you planted turned into a flower.
What matters is what your answer tells them about your judgement.
If you take responsibility and explain what changed, you give them something useful to assess. If you blame everyone else, dismiss the problem or make a vague promise, you give them another reason to worry.
“We have had projects that did not meet expectations” is only the start of an answer. The reassurance comes from explaining why, what you did about it and how that affects the way you work today.
Why can claiming perfection put your deal at risk
Imagine asking a potential supplier about a difficult project and hearing, “We never have problems.”
Would you feel reassured?
Or would you wonder whether they understood the question?
For a buyer who knows how complicated technology projects can become, that answer may feel unrealistic. And once they doubt one claim, they may start questioning the others.
Were those results typical? Were the costs complete? What else have they left out?
Small niggles become bigger worries.
This does not mean you should invent a failure to appear relatable. It means you should describe your actual experience accurately, including the limits of what you can promise.
If you have not delivered exactly this type of project before, say so. Explain the relevant experience you do have, how you will test your assumptions and which parts still need checking.
Trying to sound perfect can leave a buyer with less confidence than a clear explanation of what you know and what you still need to establish.
How should you answer when a buyer asks what went wrong
Prepare an honest answer before the question comes up. Choose an example relevant to the buyer’s concern and talk through these five points.
Explain what happened
Describe the intended result and where the project fell short. Be specific enough to make the issue understandable without exposing a customer’s confidential information.
“The migration took longer than planned and interrupted the customer’s working day” tells the buyer more than “There were a few challenges”.
Take responsibility for your part
Explain what your business could have done better. Perhaps you underestimated preparation time, failed to confirm a dependency or did not communicate clearly enough.
If several factors contributed, explain them fairly. Avoid turning your answer into a speech about how difficult the customer was.
Describe what you learned
What did the experience reveal? A gap in discovery? An assumption nobody checked? A handover that left the delivery team without crucial information?
The lesson should explain the cause, not simply repeat that the outcome was disappointing.
Show what changed
“We learned a lot” is not evidence of improvement.
Explain the change you actually made. That might be a readiness review, a named owner for each dependency or a clearer approval process before work begins.
Where you have evidence of how that change has worked since, share it accurately. Do not claim that a new checklist guarantees a problem can never happen again.
Connect the lesson to this buyer
Bring the conversation back to their business.
“That is why we want to confirm these dependencies with your team before agreeing the migration date.”
Now the buyer can see why you are asking certain questions and how the lesson informs their project. You have given them a practical reason to trust your approach.
What does an honest MSP sales answer sound like
Here is an illustrative example, rather than a reported client case study.
A buyer asks an MSP whether a Microsoft 365 migration has ever gone wrong. The MSP might answer:
“Yes. On one project, the migration took longer than planned because we had not fully checked how an older application depended on the existing setup. That caused disruption, and our preparation should have picked it up.
“We changed our discovery process to include an application dependency review before confirming the migration plan. We also agree who will test the critical applications and what needs to happen before the change goes ahead.
“For your business, I would want to complete that review with the people who use those systems before we commit to a date. Which applications would cause you the biggest problem if they were unavailable?”
That answer acknowledges the failure, explains the change and invites a useful discussion about the buyer’s risks.
It also gives the buyer something to check. They can ask to see what the review covers, who owns it and how it fits into the proposed work.
Only use an answer like this where it reflects what actually happened and how your business now operates. A convincing story about a process you do not follow will create its own problems later.
Which responses strengthen or weaken buyer confidence
Buyer concern | Response that creates doubt | More useful response |
|---|---|---|
Where has this gone wrong before? | We never have problems. | Describe a relevant example and what changed. |
Why did the project fail? | The customer was difficult. | Explain the causes and own your contribution. |
Could it happen to us? | No. You have nothing to worry about. | Explain the safeguards and the remaining risks. |
What have you learned? | We are much better now. | Show the specific change in how you work. |
What if something goes wrong? | We will sort it out. | Explain who takes ownership and how updates work. |
The aim is to help the buyer assess your business. Give them answers they can question and evidence they can examine.
Should you lead every sales conversation with a failure
No. This is not a blueprint for opening every meeting with your worst customer experience.
Start by understanding the buyer’s business and whether you can help. Discuss the outcomes they need and provide relevant evidence of your ability to deliver.
But when the conversation turns to risk, do not avoid it. If you know about a limitation that materially affects their decision, raise it while there is still time to plan around it.
For example, if the proposed timetable depends on access to systems that nobody has yet confirmed, explain that dependency before promising a completion date.
As Zig Ziglar said:
“If people like you they will listen to you, but if they trust you they’ll do business with you.”
Being likeable might keep the conversation going. Being open gives the buyer a basis for deciding whether to put their business in your hands.
How can you prepare your sales team for difficult questions
Before your next sales meeting, choose one relevant project that fell short and review it with the people who delivered it.
Agree what happened, what responsibility your business took and which changes are now in place. Make sure the sales team can explain those changes in plain English.
Check that the answer matches your current service. There is little value in promising a thorough handover if your delivery team still receives incomplete notes.
Then practise the question out loud. Can you answer calmly, without becoming defensive or disappearing into technical detail?
Finish by asking what concerns the buyer most about moving forward. Their answer may reveal that the risk you have been discussing is not their main worry at all.
Frequently asked questions about buyer trust
Will talking about a failed project lose me the sale?
It might reveal a concern that changes the buyer’s decision. However, hiding a relevant problem does not make it disappear. A clear explanation of the failure, your response and the improvements gives the buyer a fairer basis for judging whether you are right for them.
Should I name the customer involved
Usually, the lesson can be explained without naming them. Keep confidential details out of the discussion. Focus on the circumstances, your contribution and what changed, rather than using another customer’s difficulties as a sales story.
What if the customer contributed to the failure
Explain that fairly and without blame. Show how responsibilities are now agreed and checked. A buyer needs to understand what their own team must contribute, as well as what your MSP will deliver.
What if we have not fixed the underlying issue yet
Be clear about the current position. Do not describe a proposed improvement as an established process. Explain what remains unresolved and how it could affect the work being discussed. You may need to change the scope or timing before proceeding.
Build trust before asking for the commitment
Buyers can accept that things sometimes go wrong. What undermines their confidence is the feeling that you are hiding something they need to know.
Be open about where mistakes were made. Explain what you learned. Show how that learning changes the way you will work with them.
Don’t lead with it, but don’t deny it either.
Buyers aren’t stupid. Don’t treat them like they are.
If your MSP is having plenty of sales conversations but struggling to turn them into business, book a free 60-minute Sales Review. We can look at your current sales approach, where buyers may be losing confidence and what you can improve.
