top of page

Those we love most...

This article is part of the Writing to Mary and Jack series.

Dear Mary and Jack,

A few years back I was leading a team of about 30 people in challenging times. We had a business to turn around, and all eyes were on us. One of my closest allies in this experience was my Sales Director. Him and I had been working together for a while before, and forged a strong bond of mutual trust. When this new adventure started, I asked him to come and help and he accepted.

6 months into the job, there were some very promising signs that we’d started on the right track. Product/Tech, Marketing and Sales were working hand in hand. We had established an effective client feedback loop, which enabled us to nab a couple of quick wins. We translated these in higher customer engagement and very cool marketing messaging. It was going well. More to the point, sales were on target.

Despite this, 6 months into the job, he was discouraged.

At one of our weekly calls he told me straight that he was struggling with motivation. He was not quite clear yet on why, so we left the subject hanging and we did not go deeper. I was terrified at the idea that he would leave, but accepted that whatever he did, I would manage the outcome. What seemed important was to give him a bit of time and space.

Three days later, still thinking about (and reeling from) our conversation, I started wondering what I had put in our relationship which could have helped or accelerated his state of mind. I did not think: “Did I do something wrong?”. It was more along the lines of “It takes two to tango, if he is demotivated, did I contribute to it?”. No sooner had I formulated this question than I realised what was happening. “Realised” doesn’t quite capture it. I should say: “It hit me like a ton of bricks”.

He was trusting me, and somewhat non-consciously, I wasn’t trusting him. And I wasn’t trusting him, because I wasn’t trusting myself. Despite the early positive signs, I was still doubting about my ability to nurture a successful organisation. I doubted whether we’d be able to turn out something valuable, and with no lack of PR inside the group, I felt exposed.

I was feeling under pressure and I had passed it on, and applied pressure on him. It mostly took the form of direct instructions on how to do, regular questioning on the details of his activities, and the relative absence of encouragements. That was not quite micro-management, but it sure was going that way. Besides this, the absence of personal positive feedback, despite his great work, really wasn’t helping.

Because he trusted me, he took to heart what I said and didn’t say to him (Sounds obvious doesn’t it?)

... so I was really sapping the foundation of my own business.

Shortly before that time, we had had an important sales pitch close to where he lived and he had invited me to sleep over at his place. In his garden was a beautiful and solidly built garden shed, which bore the halmarks of fantastic, detailed, painstaking handiwork and planning. His whole house was, much in the same way, ingeniously arranged, his creativity, cleverness and talent were shining all over.

Creative Commons - Aaron Anderer

I had under my eyes the very proof that in questionning his work, I was in fact deeply mistaken. The next morning in the car I had made a comment along these lines: "What I have seen in your house yesterday evening was simply amazing. What makes that somehow all this talent that you have stays at home when you come to work in the morning?".

Well the answer was simple: I was discouraging it to show up.

It took him guts and trust to tell me just how he felt. The moment he opened up, it dawned on me how much courage he had. After all, if I'd felt demotivated, would I have told my own boss? Not sure. I called him back and explained to him what I’d realised, and how I felt about sales, and how I felt under pressure. That day, our relationship got unstuck.

I felt sorry, I said that much, he took it in stride, and never bore me a grudge. We went on to deliver one of the most successful years of my professional life. More than the numbers stacking up that year, that moment is the one achievement I cherish most. How somehow sincerity and trust had cut through plain human imperfection.

Dear Mary and Jack, there are countless lessons from this episode, and every time I think back about it, I still find something new to think about:

  • From knowing each another to working with one another, there was a turn in our relationship that we did not discuss, we had not discussed how we would function together. Mother nature hates a vacuum, so what was not organised between us around elevating our work, got filled with stuff that degraded it;

  • Instead of sharing my own vulnerability (See: “Who’s got our back?”) I’d shared my knowledge to better hide it. In so doing I’d treated a senior sales professional like a rookie, not because he deserved it, but because I needed it;

  • I had forgotten that words said and not said do matter, and that people I lead would pay attention;

And also:

  • Despite all this, there was enough trust in our relationship for him to tell me when it went wrong;

And finally…

It’s always those we love most that we hurt first.

so when you do, say you are sorry, it helps.

Keep well,


23 views0 comments

Recent Posts

See All


bottom of page