From Wing It to Win It: How to Prepare Like a Pro

Over the years, we have come familiar to hearing clients and fellow travellers take the ‘winging it’ approach to business development which, unsurprisingly, has yet to take off as a case study at Harvard Business School.

It may sound like a missive from the Department of the Bleeding Obvious but, the biggest buy signal is when a prospect agrees to see you. It is your job to find out why that is and what their problem is. aTurning up, ‘just for a chat’ is wasting the opportunity. This checklist is a useful primer to ensure you’ve done all you can to prepare properly.

1. Know Why You’re There

Start by writing down exactly what you want out of the meeting.

Ask yourself:

  • What’s the meeting for? Introduction? Briefing? Pitch?
  • What message do I want them to remember?
  • What’s the best-case outcome? A sale? A proposal request?
  • What’s my minimum win? A second meeting? A referral?

Get clarity. Without it, you’ll meander.

2. Prepare Smart Questions

Don’t just rock up with a few vague queries. Plan sharp, insight-driven questions that get under the skin of what the client needs – not just what they say they want. Great questions show you’ve thought about them and are genuinely curious about their business. 

3. Bring Something Useful

Have something relevant to show or share. (Note on case studies – as one client said, “showing past work…it’s like showing pictures of your children.  Lovely, but I don’t care.” So if you must, keep it relevant, keep it brief). A one-pager that makes them think. A well-chosen article. Whatever it is, make sure it adds value to them, not just visibility to you.

4. Anticipate Objections

What might stop them saying yes? Price? Speed? Fit? Prep your responses. Address concerns before they’re raised, and be ready with real, confident answers.

5. Differentiate—For Real

Why you, not the other lot? And no, “our people” isn’t good enough. Everyone says that. Be specific. What’s your real edge? Speed? Strategic clarity? Measurable impact? 

6. Spell Out the Benefits

What’s in it for them – truly? Make it tangible. Faster results, higher ROI, peace of mind. If they can’t see the value, they won’t buy.

7. Speak the Language of ROI

Don’t just pitch features. Show them the financial upside. “This will reduce downtime by 20%.” “We’ll increase lead quality, decrease cost per acquisition.” Use numbers – it is the language of business.

8. Handle Objections Like a Pro

When objections do come up, follow the KLIPS model:

  • Keep calm – no flinching.
  • Listen and learn – dig into the real issue.
  • Indicate you understand – reflect back what you’ve heard.
  • Pause – don’t rush to fill silence.
  • Solutions – respond clearly, confidently, and concisely.

And if you’re not flying solo, decide who answers what beforehand. Don’t bicker or overlap. That’s amateur hour.

9. Watch for Buying Signals

Prospects rarely shout “Sign me up!” there and then in the meeting (sadly). Instead, they give subtle cues:

  • Asking specific questions about your proposal
  • Wanting more detail
  • Asking your opinion
  • Challenging an idea (yes, even objections are engagement)

Your job is to spot these signals and act on them. Expand, clarify, guide. And if there’s radio silence – prompt them: “What stands out most to you so far?” “Is there anything you’re concerned about?”

10. Close with Confidence

Too many meetings end with “Well, thanks for your time…” followed by tumbleweed. You need a close – AKA agreement.

Here’s the top five we have found to be the most useful and don’t make you feel like an amateur dramatics’ performance of Glengarry Glenn Ross (and if you’ve never seen that film, download it tonight – it is the sharp end of selling for a living and will make you feel good about your life choices):

  • Confident Close: “We’d love to help. We can draft a proposal by Wednesday.”
  • Summary Close: “Here’s why we’re a good fit – would it be helpful to write that up?”
  • Fear Close: “If this slips, X could happen. We can outline how we can help avert that?”
  • Alternative Close: “We can send a proposal or set up scope now – what works best for you?”
  • Concession Close: “Shall we start with Phase One and revisit the rest later?”

Follow up in writing the same day and confirm the next steps.  Then stick to them.

11. Plan for Surprises

Your meeting might not go to plan. Less time, different people, tech fails. Doesn’t matter. Be ready to adapt.

The military mantra fits: anticipate everything, expect anything, assume nothing.

Final Word: Preparation = Professionalism

Prospects don’t remember bland chats. They remember clarity, confidence, and real value. If you want to win business, impress with preparation. At the very least, never open your notebook to reveal a blank sheet of paper – it’s unimpressive.

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