When trying to land investor confidence in your venture or product, how can you and your team secure higher tier buy-in from new decision makers consistently and repeatedly?

Whether you’re in the transformational leadership space, lead with an iron fist or haven’t the foggiest clue what your style is, I am going to tell you how you and your team can grow the amount of pitches won, consistently. And how you, as the leader, can develop people and process to ensure continual success around the table.

Firstly, I’ll say that I relate to the disheartening feeling of being the front runner for an opportunity, only to have it slip away. I once had to personally wear a $35,000 loss on a deal because of a $3 mixup. Long story. Still feel the tears.

But the hardest part was that I always felt the prospect had the power, like I needed them more than they needed me. I was dancing to their tune and not doing it very well. 

Feeling like this, I decided, sucked.

It took me a long time to realise that the only constants in any deal, successful or not, was my team and myself. Those variables were completely in our hands and they were the path to the securing the best outcomes, once leveraged correctly.

This article explores WHY investors and clients buy when they do, how you can both generate stronger and more ready buy-in, plus help others do the same. I’ll also cover what pre-meeting prep is often overlooked, how to structure and set a winning frame for meetings and techniques to confidently steer conversations. We are not discussing where or how to find investment, this is about the finer details of smoothing over relations and securing personal confidence from a person you want to make a decision.

Also, although this is written in a B2B capacity, many aspects cross over. Much of my experience coaching on this topic has been with senior leaders in Accountancy or Wealth Advisory, but the core principals will apply no matter your industry or target.

So whether you are the company VP of sales, running your own business or sales team, or just starting out, there will be concepts here that will hopefully help you GTM, GTFM. Look that up if you’re not sure what it means.

Have fun!

How to use this article.

There’s a LOT to cover, so give yourself the time and space to let exercises and points sink in. Ideally set a distraction free space and commit your focus. There’s also huge potential value involving your team and key people. Either way, make sure you have a coach or mentor to keep you on track and allow the thoughts somewhere to go. This is SO MUCH harder in your own head.

So, let’s get it on.

Disclaimer – This article is written for general education and informational purposes only. It is not to be considered, or used in lieu of, any specific personal, professional or financial advice.

What should we do before the first meeting with a prospect?

Know the lay of the land

This is ‘The Art of War’ 101, know thy opponent. 

Make sure your offering is market relevant, from their POV

Eg; If everyone else is using VR and 5D immersive pitching (they’re not) and you’re still rolling Excel with bar charts, your credibility could be in trouble. 

Attend a few meetings as a potential investor in your market yourself and pay attention to;

• The tech being used for display along with the quality, length and content format. Was it clear and concise?

• The length of time presenters take. When did you get bored?

• The type of language they use. Clear or muddled?

• Who warmed up the room and who iced it down?

Don’t do this with a view of copying others

Do it with a view of understanding what they say and do that grabs the attention of the prospect.

• Was there language or trade references used that you don’t?
• Did they cover points or considerations you missed?
• Did they leave things out you haven’t and for good reason?

Gauge also what the investors did. What feedback did they give? What impressed them and what didn’t? Who did they want to hear more from?

The better you know your competition and market in general, the more likely you are to win with consistency. It’s easy to sit in an office and imagine we know what our clients or investors are thinking. You don’t. You need to see them in a live setting when other people are selling something you’re not. Talk to your market.

Remember, it doesn’t matter what your competitors offering is. It will count for nought if they pitch poorly (most do) and that is where you will overtake them. Time spent here scoping the landscape is invaluable, even if you and your team are experienced.

Target the decision point, not the funding.

The goal of any pitch is NOT to get the funding, it’s to get a prospect past their trust threshold. Does your approach lead towards or away from that? Many over-complicate things to their detriment. You’re likely going to want to simplify. Complexity creates grey areas and we’re looking to build trust, which requires the opposite of complexity. 

What we’re shooting for is this concept to play out in your boardroom;

Remember a time when you walked out of a retail store having spent a small fortune and had a great experience with a sales person, even though you didn’t go in to buy?

It felt effortless, you enjoyed the experience, even if you didn’t go in to drop the coin. So why did you? 

• You were mildly curious. Even bored. But there would have been a dull spark of interest

• You browsed

• Salesperson didn’t make you want to run for the hills

• You warmed to their approach

• They respected your boundaries and were careful how much they advised and listened

• You warmed up more

• They asked great questions

• You conversed and warmed up even more…

Where’s the ‘sweet spot’ of trust in sales?

There would have been a point in the conversation where you decided deep down that you trusted them, and that’s where they had you. Doubtful you could tell when that happened exactly, but if you bought, it did. 

Somewhere deep in your brain, you said to yourself – “I trust this person”. Your feelings about them went all fuzzy and from then on, it just felt right. They suggested, you went along for the ride.

I’ll even bet you spent time talking yourself into the purchase and may the Gods help anyone who questioned you. This dynamic also plays out online, in auctions, even $2 garage sales. In any sales environment, there’s always a moment when our trust threshold is passed and we’re mentally onboard with acquiring something.

THAT is the feeling we need to build in our potential clients and investors. That sensation of trust they can’t fully explain, but they have. This is when the transaction really happens. Many skip this phase or assume it’s there, going straight for the throat thinking their figures or product can do all the talking. They don’t.

Figures and data are important, but remember, investors have played the game. They can smell bullshit. 

Exercise – Lay of the land (approx 20mins)

I want you to either remember the last time you were “around the table” or envision the next time. Whether that be just yourself, or your team, you’re in the room with a prospect and it’s ‘closing time’. Picture yourself as a fly on the wall. 

What are you and your team saying and doing? 

What are they actually achieving with their;

• Words?
• Actions?
• Body language?
• Tone? 
• Pace? 
• Intonation?
• Style?

Hint – it’s only ever one thing. 

Either the prospect is moving further towards their ‘chequebook’ or the door. You’re either building trust, or destroying it.

Which fire are your team stoking for the prospect?

Try to put yourself in the client or investors shoes as to when they might have felt that ‘sweet spot’ of trust or hit the point where they were just waiting out the clock. What was the final straw that tipped the scale? What was the journey to that point? Try to describe it or write it down from a 3rd person perspective. Give yourself the fly’s vantage-point, and remember, that fly would have seen and heard you as well.

Involve your people in this exercise as much as possible. 

Delegation and extensions of trust, build trust. Ask your people to Q/C your pre-engagement strategy. The trap here is to get stuck doing this yourself, which creates you and you alone knowing the lay of the land and your team winging it. Also, a fox can’t smell their own scent. Sometimes we are just too close to the forest to see the huge, towering fuck-up trees hanging over us.

You team can provide context and perspective you can’t see, I guarantee it.

Take this exercise and let your front end team play with it as well. What you’re looking for here is not so much their awareness of themselves, but their ability to appreciate how the PROSPECT might have perceived them. Communication after all, has NO VALUE save for how it is received.

People that close pitches consistently have a few things in common, and a big one is that they’ve developed the ability to adapt their style to engage someone else. Critically, this starts with awareness of not only how they are acting, but more critically – how other people perceive those actions.

Pro-tip; If you really want to get into this, role play it. Set-up a copy of a recent meeting when you lost the deal and run through it with your team. This can bring out language and perspectives you’ll never see any other way. The point here is to ensure you’re going into your next cold meeting not with a script, but with a knowledge of what you all do that either helps or hinders the building of trust.

What happens during the first official meeting?

If you’re pitching as a group, keep your focus on your people. 

They’ll be looking to you for calm and certainty, usually the exact things they don’t feel right now. Freak out later if you have to, but right now, remember that the quality of their communication here is hugely impacted by your state. Having your focus on your team first and the sale second will also be noticed by your prospect.

Develop a frame and stick to it.

Build a mental map of how this is going to go. The theme here is always the same. Clarity, certainty and ensuring we retain the frame control. 

This is a good go-to frame for a first meeting;

• Open with the outcome you intend to deliver and set the basic frame (time you need, any housekeeping or informative conditions)

• Ask the prospect what they would like to achieve from this time? What’s a deal breaker for them? Ask questions to engage them. What’s the end result they want from potentially engaging you?

• Reset the frame by now stating that you have a SHORT presentation, what it will cover and why. How long it will take and that after that time, you’ll let them know where to next. Yes, you’re going to spell this out and people love it.

• Present your pitch with ideally no more than 10 slides as a story demonstrating indirectly the insane value and ROI for the end user. Don’t mention this directly. The audience needs to make up their own mind. Elegance is always best when understated.

Remember: do this casually and simply. It’s NOT a university lecture. Also, keep any visual data very simple at this stage. If it takes more than 3 seconds to understand, it’s too detailed. 

Try this;

Not this;

• Use language they understand and relate to, getting into tech mode is a death sentence. Also, if you’ve spoken prior, use their own language to emphasize points. Words someone else has chosen always have more impact when used in conversation with them.

• Ensure your pitch deck includes relevant social proof, minimal core facts only and sources (Leave out your qualifications and personal opinion)

• Ensure you mention this investment is additional to your own sources. You don’t need it, but it would make things faster and more efficient if you did.

• Close with how they can proceed with you and that you only want to do this if you both feel it’s the right fit to move forward (This is you keeping the frame and NOT sounding desperate). Most importantly, give them only one avenue and a timeframe.

The goal of a cold pitch is to spark curiosity in their ROI and confidence in you with a view to a second meeting. That’s it. Too many cooks, or too much of a good thing, spoils the broth – FAST. IF you manage this and leave the room with them seeing you as a desired option, not a desperate sales team, you nailed it.

Desperation Kills – Watch your language

We can have the best product, solid data, fantastic projections, even gold-plated social proof. All of that can be destroyed in one second by the cold dagger of desperation. In ANY sales meeting, being needy is biggest killer. You want the deal. You know it. They know it. But if they feel you NEED it, it’s over.

Be careful of using phrases like these;

• We’d love to hear back from you

• We’re flexible on your options

• If you need to change this, we can

Politeness is often heard as desperation. Talk this through with your coach or mentor for best results as often it’s so well masked in our language, we can’t even see it.

Exercise – Frame Awareness (approx 45mins)

What’s your sales frame and how does the above compare? Also, if you asked your team to describe the strengths and weaknesses of the setup you run with, could they? Again, try to place your recent meeting in your mind and envision the frame you intended to use and what played out. Bullet point it.

Did we demonstrate clarity?

• Certainly?

• Confidence?

Or did we come across as needy, desperate and hopeful?

Frame control is everything guys, without it, you’re dancing to their tune. And whomever is dancing, is buying. These questions will help you understand not only a good frame, but also the clarity by which your team understands it. Because if they don’t there’s no way they’ll confidently deliver and close within it.

What do we do after the first meeting?

Quality of the initial follow-up is critical. And remember; 

Curiosity killed the cat. Desperation killed the deal. 

If you’ve got bite from the initial meeting, whenever possible follow up in person / phone / text / email – in that order. Trust is seldom built as well through digital exchange. You might be feeling the temptation to hide behind genuine contact here to avoid possible rejection. I get it, but the best deals are still made with ‘handshakes’. People do business with people, not emails or slick imagery.

If you want to build trust, make this personal. 

If in doubt and if digital is all you have, ask someone to read the email or text you’re about to send and ask them – in an investors position, would you reply to this? Digital is the fastest way to give away the frame control, because you have ZERO control over when someone responds. And when they have frame-control, you’re the one dancing. NEVER forget that.

Further involve your team 

You may have noticed a prospect warmed to certain members in your group. Guess where I’m going with this? Take the opportunity to develop and involve this person if needs must to keep a higher-quality of contact with the prospect. If your star performer isn’t on board with this, then consider checking out my other articles as well on delegation and team buy-in.

Don’t wait for the prospect to call you. 

In every correspondence, keep the frame. Always say where, when and how your next move will go down. Consistency in your approach will help offset fears they have about your ability to deliver. As if you set the standard that your time, language or approach has gaps, how secure is their investment?

How do we nail the follow-up (close) meeting?

Set the board to win

We’re past the first hurdle, now it’s time to play the real game. A few considerations for you as the leader here when setting the frame for this meeting;

If you have the option, try to match your sales team specifically to the prospect. The more you know how to read people here, the better. Sometimes the strangest of people that shouldn’t connect well, do. 

Eg; If you’re pitching to an old British crowd, having a newby on your team who thinks it’s fun to mention that Monty Python is the snake from Harry Potter, this might not win you any brownie points.

Select those that can both connect with AND challenge a prospect 

Remember, once a prospect decides that you’re a good egg, they will automatically have more faith in their investment. Nobody wants to invest with someone that can’t lead others well. The selection of people in the room is yours and this will not be lost on your client. Place people there that appeal to the needs and values of your client – and sometimes that means people that will challenge or disagree with them.

Ever noticed how a good argument can bring you closer to someone?

Don’t ever be afraid of authenticity. Most of your competition are.

Help others feel the power, always. 

Nothing sets into our minds deeply until we have to teach it to someone else. Whatever you’re considering with this meeting, try to delegate as much of it as possible. Nothing says I don’t trust you, like not trusting someone. What parts can you delegate or outsource to both advance the chances of winning this deal, but also to develop confidence or abilities in your people?

Remember, they are with you already – the prospect is not.

Your biggest adversary now awaits

It isn’t the competition or the prospect as such, but their ego. This is the challenge in sales by which all others are measured.

And this imposing 9’ tall ego clad trust warrior of raw objection stands tall and breathes heavily and derisively over you right now, even if it’s concealed behind the nicest of smiles. It’s an imposing figure with a self-protectionist agenda, but one does not simply give up, there is hope. 

Fortunately, for all its defences, this ‘trust soldier’ is somewhat predictable in its behaviour. It’s a sucker for being considered valuable. What’s your current process for ensuring an investor or valued prospect experiences your team’s presence in ways that builds personal respect and likeability?

Sounds simple, but how well do you really know them? Even finding out what someone drinks goes a long way. Remember, you’re meeting with people here, don’t let the dollar signs obscure the fact that they’ll go home tonight, probably watch Netflix, order pizza and snore badly just like the rest of us.

What small things do you do to generate the warm and fuzzies for them or are you in fact doing anything that could cause the opposite? 

This can become blazingly obvious in cross cultural or multi generational environments, but it plays out everywhere. Who is your prospect?

What’s their style, history of commercial partners and options? What do they tell you about this person? It’s worth having a simple profile built so you can then begin to understand what matters to them as a person. It deepens the possibility of rapport and relatability when used genuinely and considerately.

And genuine relatability is power.

The point here is to check that your focus in prepping for this meeting isn’t all on yourself, your logistics and your ‘amazing’ product, but on who’s buying it. Gentle and subtle considerations build trust FAST, but overdoing it kills it just as quick. Be the softly lit candle giving the room a warm ambiance over dinner, don’t try to be the 7 piece band grabbing the limelight.

Nothing says “don’t trust me” faster than saying exactly that through your try-hard, desperate actions.

Exercise – Awkward conversation anyone? (approx 20mins)

A good test is to imagine you’re all stuck in a lift that’s broken down with the prospect. Could you hold a conversation comfortably for at least an hour and cover NOTHING business related with them? 

Without getting creepy of course, can you or your team actually relate to them? What do you think they would ENJOY discussing with you? Not YOU the person wanting their investment, YOU the person stuck in the lift?

A good example of this is the old story of the sales manager for a well known manufacturing company who was trying to get a US$40m contract with Ford. So no pressure. He and his team were up against considerable odds and competition for a tender of that size, so they got creative. They found out who the decision maker was. They then found his Facebook profile and saw that the whole family were fans of a certain football team.

12 days later, a football signed by “someone very famous” just happened to find its way to the decision makers front door on a courier, complete with a business card.

Now, that shouldn’t work. And it won’t always, but this time it did. We are all people at days end and high level sales isn’t about convincing people, polished speak or flashy meetings and promises of grand results. It’s about other people deciding to trust you. Find out what leverage you need to move that dial for your next prospect and see what you could add to the polish of your engagement that is subtle, but also genuine and shows intent to value and respect their time and investment.

Treat this meeting like a first date, because it is.

And nobody wants an awkward first date, so how are you going to make it legendary?

I’ve no doubt you have a history, much like mine, of success and failures in the dating game. It’s not all pretty, but the lessons learned here come back into play. Get started the right way, with the right frame control.

When dating and trying to “impress”, if you wanted the object of your affections to call back, when did they? Did it ever happen when you were desperate?

Thought not.

Forbidden fruit has an appeal for everything but a cliche reason. If the fruit is too accessible, nobody wants it. This person wouldn’t be speaking to us if they didn’t see the value. So they’ve agreed to a first date, now it’s time to really dance. 

Here are the basics of setting frame control for a meeting;

• Make sure you set the time and location

• Be there slightly early

• Don’t wait more than 15 mins for them if they’re running late

• When you meet, set the time you’ll have to leave by and leave then

• Ensure comprehensive reconfirmation

Pro Tip – Have the client or investor do some work in advance to come to the meeting and be prepared to rebook if they drop the ball.

These apply to phone, digital and personal meetings. You hinder your chances considerably of getting a second date, regardless of what you sell, if you present as unreliable or that you’re not in control of your own schedule. So the exercise here is to ask yourself how you would feel going into a meeting as a prospect being treated with your current frame control? Does it need adjusting to make the person feel valued?

It’s worthwhile letting a bit of perspective bleed into your mind here guys as often we are so close to the forest, we can’t see the trees of the shabby, self absorbed meetings we’re holding.

Simple Communication. Less is more.

Ever heard – it’s not what you said, it’s how you said it?

Once you’re in the room again, don’t over-complicate. By now, you’ve done the hard work. They’re in for round 2. Now you want to ask as many quality questions as you can with the goal being for them to sell the idea to you, NOT for you to talk all day. 

Imagine this meeting has a theme. And the theme is, we’re going to shut the hell up.

Eg;

• Ask them what’s their best case outcome from this meeting?

• What does that outcome look like?

• The deal fails, how do they see that happening?

• Ask what that outcome needs to deliver for them?

• What do they see in us to be able to deliver that?

If you’ve got even a basic understanding of an advanced sales process and it’s been in play, at this point, you should be 99% there. The reality is, they wouldn’t be back here if they weren’t mostly sold. But it can all go wrong very quickly. How?

No doubt you know the scene?

They’re smiling.

You’re smiling.

Everything seems to be going well, until the close. Welcome to…

Your biggest problem

When does it go wrong?

Leading a team in sales is a mix of confidence, clarity and certainty all held in a tight frame of control.

• You’ve set the frame
• The deliverable isn’t in doubt
• You’ve even got some personal touches and info to help you connect with your prospect

Then, at the moment of truth, it all goes to bollocks. Why?

A prospect needs to feel trust in 3 things. Your team, the venture/product and your company. If any one of those is weak, you’re in hot water. And there is one bastard of a factor that can shatter it all in a heart-beat.

Confidence. Worse still, a lack of self confidence. Ever felt like this inside at a meeting;

All the tools and hacks in the world won’t save you if you struggle to hold a confident line of dialogue. Now don’t confuse this with “the gift of the gab” or having to be some showtime extrovert. That’s more often a hollow confidence and although it can win deals, seasoned investors recognise the snake-oil.

Any of us can have great meetings by developing the right skill set in line with trust in ourselves and team to deliver. The combination though, is incredibly powerful.

Self confidence however is a massive area for discussion and half the work of an executive coach, but I will offer some tips that I know have started working for many of my clients (and myself) wanting to boost self-confidence and add finishing touches to a sales conversation.

Never forget

We are always NURTURING the sale. Never forcing it. 

The prospect will guide you right to the door if you master rapport, frame control and ask great questions, but you will need to open it for them and that’s where your confidence in yourself will either make this deal, or shatter it.

Field tips for self confidence building

Get “kicked in the balls” for 6 weeks straight

Similar to the 100 days of rejection test, seeking out rejection over time can desensitize us to its effects. My phrasing is a tad more crude, true. But deliberately subjecting ourselves to an evil reduces its power over us. 

Change a personal boundary and own it

Self confidence is a muscle and just like at the gym, when we try to lift something too heavy, it hurts. Start small with a personal boundary, something you want to change. Once you can communicate that and hold yourself to it, the muscle will start to build.

Dance

If you can possibly find a local class, do it. There’s nothing like learning boundaries, control, mannerisms and trust in yourself than dancing. I appreciate not everyone’s cup ‘o sunshine, but if dancing isn’t directly your jam, find something that achieves the same thing. When we are dancing, we are vulnerable, in public. What can you do to strengthen your resolve to being seen and being ok with that?

Dry run low key situations

Holding a clear conversation requires practice. We can build the muscle by taking the concept and lowering the stakes. Maybe this is a chat with your partner, friend or mentor about something that requires clarity to succeed.

When in a meeting, focus on the other person

Fear loves self absorption. It’s a purely selfish, self protective emotion. Try to keep your focus on how the other person is acting, what they’re saying. Fear and doubt can only burn the logs we throw on the fire. Starve the bastard.

Ask for qualified, relevant feedback

This isn’t a solo journey. Don’t try and do this stuff alone, it’s very hard work to build a successful sales team or process. Find a mentor, coach, partner or friend that relates to you at your level and practice / discuss actively. Whether you are over confident to the point of arrogance or feel too timid to sell and convince, qualified feedback helps us appraise ourselves objectively. I promise you, you’re never as bad as you think.

Don’t face your fears, seek them out

Find a situation a couple of times a week that freaks you out, just a little. Don’t want for them to appear, find them. The power in facing a small fear is huge, the power in facing it when you’ve gone looking for it? Ten fold. You then fully own the process start to finish and the effect is magnified.

Tasks like this, when done deliberately and consciously will have two effects. They will first develop a sense of trust in yourself that you can beat something that freaks you out and even if these meetings don’t, you’ll become more calm and confident in them. 

When coupled with feedback from a coach or mentor, they will help you focus this newfound trust into the tools and techniques to give you consistent, measurable results in the sale arena and help you develop those traits in your team. They already look to you, why not improve what they already see in you?

Conclusion

There’s a reason this is a long article. Well done for getting this far! 

It’s long because our ability to lead and develop a sales team all pivots on our self confidence, how we communicate and our frame-control. All 3 are necessary and all 3 can be influenced by the work and development we undertake.

You also have a team with you and whether the next meeting (or ten) go well or not, you have them. Never forget how important those people are, or your responsibility to help develop their talents and encourage their growth.

I’m often asked, what makes a good leader? And it’s just this type of situation. 

Nothing says more about you as a leader than how you are with your people under pressure, when you win as well as when it all goes to shit.

Happy closing!

Thank you for reading!

Paul

Paul Charter is a specialty CEO coach helping leaders reach target metrics by mastering self-awareness and interpersonal communication.

You can read about Paul here, or connect with him here.