Anthony Iannarino: Technology serves what we really want, and that’s skill sets and mindsets

When it comes to sales management, Anthony Iannarino always has a plethora of useful advice. He is an acclaimed international speaker, author, and sales leader and was recently included on the 12 Sales Effectiveness Experts to Follow if You’re in Sales Operations list.

I had the pleasure of talking to Anthony and picking his brain about the elements that drive sales excellence, the role of technology in performance, and the instrumentality of sales operations in the sales ecosystem. He even shares the names of thinkers in and outside the field of sales who have influenced him. I hope you’ll enjoy reading the interview below as much as I enjoyed our conversation!


Let’s start with the basics. What one piece of advice would you give to sales managers for driving sales excellence?

Develop your people. Sales managers need to look at each individual on their team and ask themselves, “How can I best help this person reach their full potential?” You have to see the potential in other people that they can’t see in themselves. See beyond what they are not doing and identify the obstacle that stands in their way: fear, lack of skills or lack of confidence. They need somebody to help them break through.

If you want to turn in your best performance as a sales manager, you have to help the individuals on your team turn in their best performance.  From what I see, a lot of sales managers make their number and do well because the top two out of ten on their team do really well.  But your job as a leader is not to just make your number. You need the “B” and “C” players to move up. You need to figure out how you can help them. After all, you hired them, so you’re responsible for helping them succeed. It’s too easy to say, “They’re failing.” We must do the heavy lifting of helping people transform and grow.

Sales operations and sales management work together to achieve business goals. What could sales operations do to increase the value the function brings to the organization? 

Sales operations has a critical role because it can help enable three things: mindset, skill set, and toolkit. Sales management has to embrace sales operations and say, “What can they help me give these people? Where are we deficient, and how can sales operations shore that up?” That corresponds with, “How do we onboard these people? What attributes do we hire for? What attributes do we know we’re going to need to coach, train, and develop?”

The mistake is that we think, “tools first” and then we think, “people,” “skills,” and “mindset.”  I think it’s the other direction. Technology doesn’t come first. Technology always serves what we really want, and that’s skill sets and mindsets. If you would look at it through that lens, you’d see something different.

My first book, called The Only Sales Guide You’ll Ever Need, came out on October 11th. The first half is about mindset. Every time a sales operations person sees the table of contents, they go, “This is what we’ve been missing,” because it’s about discipline, optimism, caring, competitiveness, resourcefulness, and initiative. Right now, the biggest differentiator for salespeople is business acumen. If a salesperson can’t come up with the next idea and they don’t know how to solve complex problems, their business acumen will not be enabled with the right underlying attributes. This is where sales operations can make a difference.

Sales operations professionals tend to grow into their roles from other parts of the organization. You can’t get a degree in sales operations. Do you think organizations could see an opportunity for utilizing a sales operations business-process-as-a service option, especially where the business goals are robust, but they are missing key expertise?

I like the idea.  Someone who has deep subject matter expertise in sales operations can say, “I can help you develop a way to hire and onboard a certain set of attributes and skills. I can help you with the development of a plan to engage and grow people into those skills. And, I have the ability to put all this together on a sales stack with your CRM and all the supporting tools.” That’s an interesting approach.

The challenge for people in sales operations is that sometimes they come out of learning and development, and sometimes they come out of sales. But the role of sales ops is very different. Knowing how to help salespeople activate all these attributes is a different set of skills.

If you had a team of three or four people who were really good at that, you could do a lot of great work fast, because that team already knows how to do it.

We’ve had some interesting interfaces with our customers in the past couple of years that drove the creation of our Sales Operations as a Service offering. As you yourself said, it’s not the technology that brings the greatest value in many cases – it’s the ability to fill in those gaps related to process and expertise.

Look at what we do in sales. We have people right now who are Acting Vice President of Sales, and we augment that role with an RVP when we need to. We augment training.  We do it in lots of other roles. Sales operations is not any different.

When you look at sales performance, what’s behind the numbers?  And, how do you affect those things? There was an Air Force Colonel named John Boyd who worked on the F-15 and F-16 and who used to testify in front of Congress and speak to the Pentagon all the time. He would just tell them, “people, ideas, technology.” It’s people, ideas, and then technology.  Technology should enable all those things that you want from people and ideas.

I think the expansion of Optymyze into a Sales Operations as a Service offering is natural, because somebody’s saying, “You’ve helped so well with this part of it. Can you help us with the other part?”

We also find that another piece that’s not related to technology is the understandability around a compensation plan. Do you think that sales leaders do a good job of making sure salespeople fully grasp the plan?

I think we change too frequently, and we don’t give people enough time to understand what they need to do. I’ve seen sales organizations that change their compensation structure and their bonus plan every year. When you have a long sales cycle, especially in complex B2B sales, a year is not enough to actuate all the things in the plan. I wouldn’t say sales managers are guilty of not explaining it well enough. When you explain the compensation plan to a sales rep, they may intellectually understand it. But it takes a lot to figure out how to do that in the field with real prospects and how to get new outcomes. We simply need to give people more time.

When organizations change compensation plans, they want to drive certain behaviors.  That’s one lever of how you get a behavioral change. The other levers are asking the sales force to do something different, holding them accountable for different outcomes, giving them additional coaching, asking their sales manager to be in the field with their reps, and making sure that salespeople can actually execute. There are other levers to pull besides compensation.

This is really interesting. I’m curious to find out, as a leader and influencer in sales management, who influences you and why?

From a sales perspective, the individual that had the greatest impact on my thinking is Neil Rackham, and not because of SPIN Selling, even though there are three pages in there that radically changed my sales results, starting on page 67.  The books that came after that, Major Account Sales Strategy and Rethinking the Sales Force, were so useful to me! Also, Mack Hanan, who wrote Consultative Selling was a big influence.

From a sales management point of view, I have to point to my friend, David Brock, from Partners in Excellence.  Whenever I have a sales management issue, I call Dave. Within 25 minutes, I have an answer and a plan because his thinking is based on so much experience and so complete.

A lot of the things I read are outside of our domain. It’s more interesting to pull in ideas on psychology, philosophy, and marketing because what we do all has human beings on the other side. I spend a lot of time thinking about the question, “How do you help people change, and what do you give them?” I recommend Ken Wilber, who’s a philosopher and studies developmental psychology; Robert Kegan, from Harvard, who wrote Immunity to Change and In Over our Heads, and Stephen Covey, who wrote The 7 Habits of Highly Effective People.  Those are the people who had the greatest influence on my thinking.

You can find more useful advice in Anthony’s new book The Only Sales Guide You’ll Ever Need, now available to order.

Make Complexity Work: How to Turn ICM into a Competitive Advantage

With so many moving parts, managing incentive compensation is complicated. But the best ICM plans are those that embrace complexity and turn it into opportunity.

Get it here

Leslie Stefanik

Vice President, Digital Marketing

Leslie is a B2B marketing executive focused on tying strategic marketing initiatives to corporate objectives through branding, revenue marketing, and media and analyst relations.

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