Sales strategy for founders: 7 questions to ask when growth slows

When sales slow down, it is tempting to push harder. More outreach, more marketing activity, more pressure on the team.

Before increasing the effort, step back and examine what has changed.

Your customers’ priorities may have shifted. Your message may no longer reflect the problem they most want to solve. Or the approach that won your first customers may be difficult for anyone else to repeat.

A sales strategy review helps you decide where to focus. These seven questions give you a starting point.

1. Who are your best customers now?

The customers you originally expected to serve may be different from those who get the most value from your business today.

Look at the customers who buy, stay and are worthwhile to serve. What do they have in common?

Consider their circumstances, the problems they face and what prompted them to act.

Also examine the customers who require extensive support, negotiate heavily or leave quickly. Are you attracting businesses whose needs you cannot serve well?

“Small technology companies” is a broad audience. “Growing software businesses whose founders can no longer manage every customer relationship themselves” describes a situation you can investigate.

Be specific enough to make choices about whom to approach and whom to leave out.

2. What makes the problem important enough to act on?

A prospect can recognise a problem without being ready to spend money solving it.

Ask what the problem costs them in time, money, missed opportunities or frustration. Find out what happens if they do nothing and what might move it up their list of priorities.

Talk to customers about the circumstances surrounding their purchase. What changed? Why did they act then? What alternatives did they consider?

For a business customer, the person using your product may also be different from the person approving the budget. Understand what matters to each.

These conversations help you distinguish a problem people find interesting from one they are prepared to address.

3. Does your message reflect what customers value?

Read your website, sales emails and pitch materials from the customer’s perspective.

Can they quickly understand who you help, what you help them do and why that matters?

Founders can become so familiar with their product that they describe its features without explaining the value. “A dashboard with automated reporting” leaves the buyer to work out why they should care. “See which customer accounts need attention before renewal” gives them a more concrete reason to listen, provided your product delivers that result.

Use the language customers use to describe their situation. Support claims with evidence you can stand behind.

If people repeatedly misunderstand your offer, examine the message before assuming they are the wrong audience.

4. Where does the buying process get stuck?

Map the steps between someone first hearing about you and becoming a customer.

Where do conversations stop moving?

A shortage of initial conversations suggests different questions from a large number of proposals that never close. Deals that stall after a successful demonstration may involve budget, internal agreement, procurement or an unclear reason to act.

Review a few recent wins, losses and decisions that went nowhere. Ask what happened at each stage rather than relying on a general impression that “sales are difficult”.

Agree a useful next step with prospects. Another follow-up email is unlikely to help if neither side knows what needs to happen next.

5. Are you reaching people in ways they trust?

Your preferred way of communicating may not be how customers find help.

Ask recent customers where they first heard about you, what they looked at before making contact and whose opinion influenced them.

That may point towards introductions, industry communities, useful articles, events or partnerships.

It may also reveal that a channel you spend heavily on plays little part in the buying decision.

Choose a small number of approaches to test. Be clear about the audience, the message and what would count as meaningful progress.

If you are considering a partner, establish why the relationship would be useful to them as well as to you. Access to an audience is only valuable if there is a relevant reason for an introduction.

6. What still depends on you as the founder?

If you win most of the business yourself, examine what happens in those conversations.

You may draw on experience, credibility or knowledge that your sales team cannot yet access. You may also make promises or agree exceptions that others would not know they could offer.

Review calls together, where appropriate and with permission. Write down the questions you ask, the objections you hear and the reasons customers decide to buy.

Then clarify what the team can decide independently, including pricing boundaries and when you need to become involved.

Hiring a salesperson is easier to justify when you understand the work you are asking them to take on and the support they will need.

7. What will you change first, and how will you judge it?

A review can produce a long list of possible improvements. Trying all of them at once makes it difficult to understand what helped.

Choose the most important uncertainty and design a focused test.

For example, you might believe that your offer appeals to companies that are too early to buy. You could test a more specific message with businesses at a later stage, then examine the quality of the conversations and whether they progress.

Match the review period to your sales cycle. A business with a long buying process will need to look at intermediate progress before it can judge revenue results.

Decide who owns the test, what evidence you will collect and when you will review it.

Start with a few honest conversations

You do not need to rebuild your entire sales strategy before learning something useful.

Speak to a recent customer, a customer who left and a prospect who decided not to proceed. Ask about their experience without immediately defending your approach or trying to restart the sale.

Compare what they tell you with the assumptions behind your current plan.

Then choose one change worth making. That might be a narrower audience, a clearer message or a better way to help a buyer reach a decision.

Space to think through your growth decisions

Sales questions often lead to wider founder questions: where to focus, what to stop doing, whom to hire and how much of the business should still depend on you.

I coach and mentor founders as they work through these decisions, bringing experience from building and exiting two technology businesses.

If you would value someone alongside you while you examine what needs to change, explore how we can work together.

Cheers,

Duncan