Early in my Sales Career I was taught one of the most important lessons in my entire career. It wasn’t by a Sales Manager. It was by my customer.
I politely asked a CEO if he would sponsor an executive briefing so we could present our strategy for healthcare to an entire province. His response was “understand my business and bring value. I don’t care what your strategy is, help us implement our strategy not yours, then I will make all the time for you”. Several months and many meetings later, the outcome was the briefing as requested, where the CIO of the province at the end stood up and said that we were the only organization that actually listened and hit the mark. That ultimately resulted in a global first solution in the healthcare industry, which was replicated in other markets. If those customers read this, thank you.
Strategic wins don’t necessarily come from pitch decks. They come from learning, conversations and discussion about the business. Raise your game.
Listen to your customers. Ask good questions. Tailor your discussion to your audience.
If you treat your customers like a transaction, they will treat you like one. Why would you expect them to respond differently?
A light switch doesn’t go off one day and you become a Trusted Advisor sales rep. It doesn’t come in product playbooks or whitepapers. If your reps continually lead with product you will never get there.
According to research from the Harvard Business Review, only 18% of sales reps are viewed by buyers as trusted advisors.
There is a massive disconnect between what buyers expect and what they experience:
- High Demand: Approximately 79% to 87% of B2B buyers state it is “absolutely critical” or “very important” to interact with a salesperson who acts as a trusted advisor rather than just a vendor.
- Low Execution: Despite this demand, nearly 58% of buyers report that their meetings with sales reps add no value to the buying process.
- Credibility Issues: Research shows that 82% of buyers prioritize a rep’s credibility over their likability, yet many reps remain focused on “rapport building” rather than solving deep business problems. That may work in a smaller market where relationships are tight however more difficult in large Enterprise Markets. Fundamentally I do believe that the likeability factor does have some impact and will get you in the door. It’s up to you whether they let you back in. Be authentic and genuine.
In an AI world, most transactional sales activities will be automated. Every company should have a learning path for their reps to become a trusted advisor. Most sales managers that have lived in transactional organizations aren’t equipped with the knowledge or experience to do that. Training programs are geared to an overload of process and product information.
Here’s how you start
Sell with curiosity, not fear of rejection or failure. Be genuine, authentic.
Find your account that drives your passion or hobby that you like to dabble in.If you enjoy investing as a hobby, pick a bank or financial institution. Find that purpose. A good manager will work with you to help find those accounts. Be authentic and honest with yourself, otherwise you are not setting yourself or the company up for success.
Even if there is a broad base of SMB accounts you can usually put them in vertical buckets. I have always been a proponent of verticalization. It builds credibility and knowledge.
For me, it started in one hospital in a small province calling on the IT department next to the morgue. For those that don’t know the IT departments of hospitals of the past could often be found in the basement. My customers were a CIO, Director of Diagnostic Imaging , and an IT Manager who were out of the box thinkers. I just followed their lead.(Thank you to them D.,G.,C).
I ended up spending close to 13 years seeing where technology made a difference in people’s lives in some of the biggest hospitals in Canada.At one point I led the Canadian Digital Hospital Strategy for one of the largest medical companies on the globe, creating some innovative firsts in both consulting and solutions along the way.
Adopt a Business Mindset
If your customer is a publicly traded company, know their stock price. Revisit it on a quarterly basis to see how they are doing. Read their investment relations and go through their investor presentations. Attend Industry events and read industry information. If you are able to secure a meeting, attend in person not remotely.
If it’s public sector read their strategic documents, know what their priorities are high level and how they are measured eg. hospital wait times, etc.
Once you adopt a business mindset, others in your own company will find you for different roles and opportunities. In my experience those people are often in leadership positions or at least on the radar to get there.
Build a Strategic Plan for one or two of your customers whether you are asked to or not. A list of accounts is not a plan. Set up an internal meeting to your broader team and present the plan on how you will help make them successful. Seek their input. It is a team effort.
Company and Manager Support
Manager support is important. Based on the statistics above that 18% ever the reality is that most managers have never done it based on the metrics and default back to what they know and are comfortable with.
“AI isn’t replacing human coaches—it’s amplifying them,” said Dr. Amit Mohindra, Distinguished Principal Research Fellow, The Conference Board.Oct 22, 2025
Companies should be on board to make this happen if they are preparing for the future. If they aren’t then it’s your responsibility to prepare to build your own career path for where sales is going. Companies that are heavenly transactional focused are not likely to be the place for you unless they have a strategy. I have made a bad decision or two over the years and joined organizations that were not a good fit. It happens. The difference this time is AI will be replacing the transactional ones.
The companies that don’t will have challenges staying relevant for thought leadership and stuck on the hamster wheel of reactive low margin transactions and unpredictable pipelines.
Charley