7 Common Mistakes Investment Salespeople Make — And How to Fix Them

If you’re in investment sales, you’re no doubt already familiar with the prolonged, high-stakes, high-pressure environment that is common within the industry. Whether you’re early in your career or a seasoned professional, we all feel the heat every now and again. We all slip up, make mistakes, and, hopefully, learn from them.

There’s no avoiding making mistakes every now and then. Unfortunately, time and time again salespeople and sales teams make a series of similar mistakes that suppresses their results and squanders valuable resources. Irreplaceable time and effort is taken away. 

At Dakota we’ve been fundraising since 2006, started hiring salespeople in 2008, and since then, we've raised over $40B.

However, this was not without our fair share of mistakes, trial, and error. 

In this article, we are going to cover the seven most common mistakes many experienced investment management sales professionals make, and what you and your firm can do to avoid these obstacles. By the end, you’ll have a clear idea of the next steps you and your team can take to avoid wasting time and money, and drive more business. 

Mistake #1: Failure to set accurate expectations 

No matter how much money you can raise, if the CEO, PM or head of sales has unrealistic ideas about how much can be raised how quickly, it only creates stress, tension, and disappointment. Not the ideal environment for peak sales performance – or for retaining good salespeople.

How to fix it: Be as transparent as possible

When it comes to sales, it’s important to set clear, measurable goals early. If you aren’t setting goals and communicating them to your boss, PM, head of sales, etc., you are most likely setting yourself up for failure. 

Instead, make it a habit to communicate and agree upon goals at the outset of a relationship, and report against that goal frequently. This will help you avoid surprises and build trust as you go.

Mistake #2: Not targeting the right channels

Salespeople love to brag about not taking “no” for an answer. But we believe “no’s” are an indication you’re not getting in front of the right buyers with the right product. 

We say: Don’t waste your effort fighting with “no’s” – seek out more “yes’s” by targeting the right channels.  

How to fix it: Stop being in the convincing business

Knowing how to take “no” for an answer is part of being an effective sales person. There is far more success to be had by knowing the right channels, than by trying to convince the wrong ones. 

We’ve put this into practice at Dakota, and part of our sales ethos is “sell apples to apple buyers.” In short: don’t waste time convincing orange buyers they might like an apple. 

Mistake #3: Not knowing and growing the Total Addressable Market (TAM)

Salespeople always want to be better at selling – which is the far end of the pipeline. But we have found that the real key to success in this business is how you feed the pipeline at its source. This is why I believe you need to be obsessed with your TAM, with the penetration of your TAM, and with tracking the growth of your TAM. Feed your pipeline and it will feed you

How to fix it: Understand your TAM

The best way forward to sales success is knowing your audience. If you aren’t sure exactly what this is and how it relates to sales, we have a complete guide to TAM that will get your started on the right foot.

Knowing your TAM and executing against it will save you time in the long run, because you won’t be wasting your days wondering who to call on. Instead, you’ll be able to work your way down a list of qualified prospects, and turn them from just prospects into leads and sales. 

Mistake #4: Failure to use Story to Bring Your Pitch to Life

People relate to, are moved, and remember storiesnot by piling on tons of forgettable facts and facts and figures. Think your product doesn’t have a story? I assure you that it does and I can show you how to find it. (Further in this letter, I’ll tell you one of my favorite and shortest examples of an investment story.) 

How to fix it: Become a master storyteller 

What makes you and your firm unique? What do you bring to the table that sets you apart? This is where you want to hone in. Find a part of your firm’s story that stands out, and delve into it. Anyone can make a sales pitch, but not every sales pitch is memorable. 

Not sure where to start when it comes to storytelling? We’ve got you

Mistake #5: Failure to Completely Control the Meeting

If you aren’t in control of the meeting, that means it’s either being controlled by the prospect or literally out of control. 

Either way, that’s certainly not how you get what you need to optimize results. The good news is that prospects actually prefer that you control the meeting – if you do it correctly with the right kind of preparation. 

How to fix it: Know what to say 

It’s one thing to work to get a meeting with a prospect. It’s another to lead the meeting, make an impact, and build a relationship from there. If you’re not prepared going in, or open with a long monologue instead of starting a conversation, it’s likely to go off the rails. 

Instead, ensure that you know what to say. Learn about the prospect, prepare a short opening that answers the most commonly asked questions, and most importantly, start a dialogue. 

Mistake #6: Settling for “Great Meeting”

Too many salespeople return to the office happy to have had a “great meeting.” But we deem any new prospect meeting a failure if it doesn’t uncover:

1. If and when they will be doing a search in your asset class

2. What the next step should be. This is why knowing the right questions – and knowing how to ask them – is such a critical skill. 

How to fix it: Make a plan to follow-up

We all want to think our meetings were great. But if you leave someone’s office with a goodbye and a “great meeting,” the relationship is likely to end then and there. Instead, plan to follow-up directly after the meeting, and build out a plan to continue following up over time. This helps give both parties actionable next steps, and keeps communication open. 

At Dakota, we like to say that no meeting is “great” unless you left with a wire of millions of dollars. Which, as we all know, does not happen. So while “great meeting,” is a nice sentiment, it’s just that: a sentiment. 

Mistake #7: Failure to Log and Utilize What is Learned 

Anything uncovered in a meeting that doesn’t get entered into a CRM is worthless. 

Why? Because unless it’s in a CRM it can’t be used to trigger sales ideas, opportunities and actions. Fortunately, today’s technology makes it easier than ever for even the most technophobic salesperson to do it – with the right kind of training and motivation. Yet it’s surprising how few companies take advantage of this. 

How to fix it: Create a killer follow-up system 

Above, we mentioned the importance of following-up after a meeting. Now, we’re encouraging you to take it a step further. Create a killer follow-up system that allows you to stay on top of everyone you’ve met within the last 30-, 60-, and 90-days, so that nothing falls through the cracks. 

We've got a step-by-step methodology that will help you do just that. 

What to do next

If any of these ring true for you, don’t worry — we’ve all been there. Start by knowing who to call on. Once you know who you should be reaching out to, you can finesse your messaging and storytelling, and work on building out your follow-up system. 

If you’re not sure where to start, or want further insight on any of the above, schedule a 15-minute consultation, we’d love to see how the Dakota team might work with you. 

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Written By: Gui Costin, Founder, CEO

Gui Costin is the Founder and CEO of Dakota.


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