Three things keeping CEOs and Sales Leaders up at night

I’m constantly speaking to CEOs and sales leaders from across the world about their growth challenges and objectives – sharing ideas and insights that dramatically accelerate their and their team’s success. I love it. Totally rewarding.

And, what’s really interesting is how often these conversations are repeated…whether they happen with potential clients in London, Toronto or San Francisco.

These CEOs and sales leaders are frustrated by three things.

  1. There’s lots of prospecting without results
  2. Sales cycles that take far too long
  3. Even when they get to the proposal stage they aren’t getting enough wins.

If that sounds familiar to you I’m going to tell you why.

  1. Your messaging is backwards
  2. Your salespeople are prospecting to the wrong level
  3. They don’t know how to write a proper prospecting letter, email or LinkedIn message that gets the people who can say “yes” excited to meet them.

If you want to improve how your sales teams perform, then maybe it’s time for a chat. Send me a quick email and let’s have the conversation or call me on +1 647 402 2096

How to Get Meetings with CEOs

In today’s hyper-competitive market, what are your new business sales hunters doing differently to accelerate your sales cycle and improve your win rates?

If they’re anything like the growth leaders I work with, they’re making sure their salespeople are prospecting to and speaking with the person who can say yes to what you sell – the ultimate decision maker: the CEO or their designated senior executive.

Most salespeople claim they’re proficient at getting meetings with C-level executives. If I had a dollar for every CV I’ve read that makes this claim…

If that were true, CEOs and other senior executives would do nothing but be in meetings with salespeople. Clearly, this isn’t the case.

So, for those sales leaders who focus their team on getting meetings and having conversations at the highest level, there is an opportunity for significant competitive advantage.

And, if most sales leaders were being candid, they’d admit they’re probably not proficient at getting meetings at this level either – and that’s why most of their salespeople spend their time prospecting to mid-level executives, because they model what their leaders know, do, and expect.

Getting meetings with C-level execs or their senior designate isn’t hard. In fact, it’s often much, much quicker to get an appointment with (or referral from) the CEO than getting a meeting with a mid-ranking exec who is vested in the status quo. This applies in all B2B sales – even if the CEO isn’t the main buyer for the product, service, or solution you sell.

It just takes a mindset tweak and some new skills. Even first-time salespeople can get amazing results very quickly when they know how.

“My first CEO response was under one minute after sending my message!” Nate, Sales Development Representative

“My Senior Enterprise Director has been trying to get into this account for years. I just got a meeting with the VP Operations in six minutes.” Cody, Business Development Associate

So can more experienced sales reps.

“I secured a meeting with a hard-to-reach CEO in 26 minutes and had a meaningful pitch to another client I was trying to engage for 18 months!” Kevin, Sr. Manager, Business Development

“I spent two years with one of my prospects without any response using the old mindset of approaching mid-level managers. After the session, the result was amazing: CEO meeting in nine hours after one email with no follow-up.” Samer, Client Partner

There are three things you can do so your new business sales team gets results like these.

#1: Make sure your value proposition focuses on the outcomes and impact your client can expect – and that other clients get – because of working with you. Rather than saying, “We help companies to…” (which is how most value props start, and why they sound the same) demonstrate immediate credibility and social proof by saying, “Clients like ABC and XYZ say they get (results/outcome/impact) because they choose to work with [name of your company].” “Choose to work with [name of your company]” is actually an embedded suggestion that pre-conditions your potential customer to choose to work with you.

#2: Go high! Once your messaging is more client focused, just switching your attention on getting meetings with more senior executives will mean you get meetings with more senior executives – as senior executives are always on the lookout for new initiatives that will accelerate time to market, increase revenue, decrease costs, improve efficiencies, and more. They’re wired that way. And research shows they appreciate salespeople who bring new ideas to them.

#3: Teach your salespeople to write well or share messages that work. Ask your sales team to send you the prospecting emails/letters that generate the most meetings for them. Tweak them to appeal to senior execs’ motivations and share the best ones with everyone so they’re not reinventing the wheel every day (otherwise, you’re paying your expensive salespeople to be copywriters).

Doing these three things has helped new business salespeople increase the number of appointments they get by 23%-400% percent. Even more importantly, appointment to opportunity conversion improves by as much as 94% and pipeline value increases by as much as 166%. And, because these are conversations with true decision makers, salespeople sell more in less time.

If you want to cut through the clutter and fill your sales pipeline with quality opportunities, you must approach prospecting differently than you may be doing today. In the words of Mark Twain:

Whenever you find that you’re on the side of the majority, it’s time to pause and reflect.”

And, if you want to accelerate the process, contact me at or +1 647-402-2096. I’ll be happy to share some additional ideas and insights.

And, if you found this article helpful and valuable, please share it with your network on LinkedIn, Twitter and Facebook. Thank you.

Matt Conway is an advisor, executive coach and speaker on go-to-market strategy and sales acceleration. Clients who work with him say they dramatically accelerate their time-to-market, revenue, and sales cycles; and improve their win rates. Matt is a 2018 Selling Power Magazine Leading Sales Consultant.

CEOs and Sales Leaders: Are your BDRs/SDRs becoming less effective?

In his article Martin E. Stevens raises the question if the SDR/BDR funstion has had it’s day.

SDR’s have, arguably, had their day. Buyers are becoming increasingly immune to their mass market, un-personalised (or barely semi-personalised) outreach. If they do engage a prospect, there are complaints about a lack of business acumen (SDR’s have mostly morphed into a low paying entry level sales positions) and poor narrative where an SDR is only comfortable talking about themselves and their own products. Meanwhile management are beginning to complain that SDR’s are driving up the cost of customer acquisition rather than decreasing it…

A client of mine decided to tackle this issue head on – move away from semi-personalised seller focused messaging to outcome and customer focused business messaging to get meetings with or referrals from C level executives (that raised the business acumen of SDRs at the same time). Look at the difference in opportunities and pipeline created!

Show Rate (18.6% increase)

• Q1: 72%

• Q2: 85%

Appointments Set (2.4% increase)

• Q1: 250

• Q2: 256

Opportunities Created from Set Appointments (94.34% increase)

• Q1: 53

• Q2: 103

Pipeline (166.67% increase)

• Q1: $2.4 Million

• Q2: $6.4 Million

If you’d like to explore if your team can achieve similar, immediate results, email me at: or call me on +1 647-402-2096 to schedule a conversation.

NO MIND READING! Advanced Discovery Skill (that builds a ‘case for change’​)

The most successful sales people that I’ve met or coach do something really well that separates them from the rest of their average performing peers. They are masters of asking CLARIFICATION questions. Clarification questions elevate sales conversations to Jedi level.

The very act of asking a good clarification questions creates value for the buyer and connects them at an emotional level with the seller. Here’s how.

Average sales conversations are an exchange of surface level questions and answers between buyer and seller. The salesperson asks basic contextual questions like “how many, how long, what platform, what’s working, what’s not working, what are your pains etc etc.” The issue with these questions is that they DO NOT create value for the buyer, because these are questions that the client already knows the answer to and it doesn’t cause them to think deeply or differently about their business. These surface level questions just get them to regurgitate answers to what they know – answers that are already conscious of (see Neocortex below).

When a client says something to the effect of “our results are not where we want them,” an average sales person will just blindly ACCEPT that statement as self evident (they ‘mindread’ what the statement means from their perspective, not the clients) and move onto the next pre-prepared question on their list to cover off, or shift to PITCHING, leaping on the client’s ‘confession’ with a “we can help with that, let me tell you how we can.”

A top performer will “slow down, to speed up” – asking “what are your results today…and what do you want them to be?” – “in what timescale?” – “what’s the $ value of that difference”? – “tell me, what’s your sense as to the root cause of the results you’re getting?” – “if this is addressed, what would that allow you to do with your business that you can’t do today?” – “and when you say ‘our results’ who else on your team is concerned about this topic?”

In the process, the seller has helped guide the client to articulating THEIR business case (or case for change) and generated thought processes that the client probably hasn’t thought about with as much rigour (Limbic brain) creating trust and value along the way (Reptilian Brain). Oh, and urgency.

In conversations with CEOs and Sales Leaders, most express their frustration that the majority of their sales people can’t or don’t do what I’ve outlined above.

The real issue at hand is that many CEO/Sales Leaders can’t/don’t do it either – and therefore it doesn’t become expected or embedded in the company’s sales approach.

So, if you’re a CEO or Sales Leader reading this and you’ve been seeing, hearing or experiencing this issue for over 30 days and feel that lack of questioning rigour is causing you to lose deals or have longer sales cycles, then perhaps it’s time for a chat?

If you want to learn more, feel free to email me at or call me on +1 647-402-2096.