Real People, Real Trust: A Fresh Perspective on Sales Operations

Anna Dutton is a Sales Operations Director for Blackboard, a company that brings technology to the world of education. Find out what Anna sees as the distinguishing traits of a trusted advisor, and learn two concrete steps she recommends for anyone who wants to bring more transparency and trust to their business relationships.

In a Word: Genuine

Anna (pronounced “Ahna”) and I met in 2009 when she was leading a team of 10 inside salespeople and wanted to share the principles of Trust-Based Selling with the group. In our exploratory conversations, Anna’s thoughtfulness, poise, authenticity, and commitment to people being the best they can be really shined through. Anna has the world at her fingertips— she has 15 years of business experience in roles as diverse as banking, tourism, and human resources, and she speaks three languages fluently. Yet she is as down-to-earth as they come.

I began my Real People, Real Trust interview with Anna the same way I began my conversation with others I’ve featured, by asking a simple question: What does it take to be a trusted advisor? Without a moment of hesitation, Anna said, “Being genuine.”

“Genuine for me means not being afraid to tell the truth, to say what you think, to say something that others may not agree with. It’s about really having integrity with the people you have relationships with.

“Most of my colleagues and former team members would probably tell you that I will always say the truth and not hide from it.  I want them to know they can rely on me, they can be honest with me, and that I always have their back. This extends into my personal life, too. It’s important for people to know where I’m coming from and that I will always meet them halfway.”

Delivery Matters

Anna emphasized the difference that delivery makes.

“Of course, I always consider how to say things. Delivery makes a difference. People have come to count on an expression I often use: ‘I’m sorry I just have to be blunt.’ They laugh now when they hear it, which brings some levity to what might otherwise be a tense conversation.

“Here’s what I’ve noticed over the years: I have never had someone say, ‘I wish you hadn’t told me that.’ I will apologize for being so transparent, but I will never need to apologize for saying the truth.

“I changed roles a few months ago, and had an exit dinner with my team. They said, ‘We trusted you; we knew you always had our back.’ The irony was that they further created that trust amongst themselves and strengthened their ties so much that they could focus on helping each other excel and succeed.  Projects and deliveries and tasks aside, this is what matters in life.”

The Courage to Stay the Course

Anna spoke to me in her characteristically frank way about the courage it takes to live from the principle of transparency.

“When you’re committed to telling the truth, you have to accept that some people won’t like it, and that not everyone will be willing to take the journey with you. Courage is being willing to take the risk and accept the consequences. Ironically, when you do that, you realize the consequences aren’t so bad. Truth-telling not only forges stronger relationships, but people respect you more, and ultimately, they thank you.

“I’m not saying it’s easy. I always have to remind myself that the benefits outweigh the negatives, and remind myself that I won’t stand for anything less. I definitely have my share of vulnerable moments. When I can remember what’s lost by not being genuine in this way, I know it’s worth the risk.”

The Journey

Anna attributes the learning of these important lessons to her own personal experiences, as well as people in her life who have served as role models, like one boss who stands out as a real trusted advisor. “I was so sad when he retired last year, but I take his lessons with me every day,” she says. Anna has also learned a lot from living and traveling all over the world.

“I had an atypical upbringing: being a first generation American and growing up in Italy, Spain, and the States.  I often related to different cultures, different people, and different perspectives.  I had to take risks to create relationships and to connect with my changing world. Life taught me many lessons, and I went from child afraid to say what she thought to someone who can, as a direct result of facing life’s challenges.”

Anna continues, “I also think that being great at relationships requires being a dedicated student of relationships. I’ve read a lot, learned a lot from experts, and I’m friends with people who are psychologist and organizational development experts. Our dinner parties are often marked by spirited and thoughtful conversations about human dynamics.”

(By the way, two books Anna highly recommends are A Fortune-Teller Told Me: Earthbound Travels in the Far East by Tiziano Terzani—a book that reinforces how just changing how you do things can cause dramatic changes in the world around you—and Type Talk at Work: How the 16 Personality Types Determine Your Success on the Job by Otto Kroeger with Janet M. Thuesen and Hile Rutledge, which emphasizes the importance of knowing your audience and how you communicate.)

Best Advice in Two Steps

I asked Anna what advice she had for anyone wanting to bring more transparency and trust to their business relationships. She suggested two concrete steps:

1.      Write down what you’re afraid of and really be honest with yourself. “Understand why you’re afraid of these things. Do whatever work you need to figure it out and address it—talk with friends, go to therapy, whatever. You have to understand what’s underneath it first.  You can’t create trust if you have fear.”

2.      While you’re figuring it out, just tell the truth for a week without coloring or altering and see what happens. “Worst case: you may annoy some folks, and see that they will not join you. I’m not suggesting you tell someone ‘You’re a horrid person’; you might say something like, ‘This situation is not working and this is why’ or ‘I’m nervous about this engagement and this is why.”

Anna says, “Being a trusted advisor is a process; it’s not like you learn it and then—boom—you do it every day. Plus as you evolve as a person, as you develop and grow, your approach may change. You’ll have bad weeks, and good weeks.  But more than anything, it’s a philosophy, an approach to life.”

Connect with Anna on LinkedIn.


The Real People, Real Trust series offers an insider view into the challenges, successes, and make-it-or-break-it moments of people from all corners of the world who are leading with trust. Check out our prior posts: read about Chip Grizzard, a CEO You Should Know and Ralph Catillo: How One Account Executive Stands Apart.

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Trackbacks & Pingbacks

  1. […] out how Anna Dutton, Sales Operations Director, finds the courage at her educational tech company to be genuine, tell the truth, and say things that others might not agree […]

  2. […] “Real People, Real Trust: A Fresh Perspective on Sales Operations” was first published on the Trust Matters blog. […]

  3. […] The Real People, Real Trust series offers an insider view into the challenges, successes, and make-it-or-break-it moments of people from all corners of the world who are leading with trust. Check out our prior posts: read about Chip Grizzard, a CEO You Should Know; Ralph Catillo: How One Account Executive Stands Apart; and Anna Dutton: A Fresh Perspective on Sales Operations. […]

  4. […] does it take to be a trusted advisor?” Heber’s immediate response was remarkably similar to Anna Dutton’s; he said, “Above all else, you need to be sincere and […]

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