On-Boarding: A disaster narrowly averted

I’m making a career move. I will shortly be leaving a (wonderful) company, for a great opportunity at another (amazing) company. A couple of weeks ago, I shared this news with my youngest son. He Said “Congrats Dad! That’s so exciting. It’s kind of like going to a new school. New teachers. New friends. New classes. You’ll have to figure out how to get there … which bus to take. Are you nervous?”

I told him that I had a few butterflies in my stomach, but that I had learned from experience that butterflies were a good thing. I was — I am — the good kind of nervous. But his comments and question got me thinking. What should I be nervous about? It’s been a while since I’ve made a move like this. What will my first days be like? After spending the last six years interviewing and hiring countless people, now it would be my turn to be… wait for it… onboarded.

Onboarded. It’s not such a warm and fuzzy term. It doesn’t scream “Get ready to do the best work of your life,” or “We’re so excited to have you! Let’s get you set up, so you’ll feel all set and like part of the family,” or even, “We want you to feel safe. We know this might be a lot of change for you and your family and we want you to know that we got you.”

Now, this post isn’t about what we should call this process (but please: throw your ideas into the comments section if you have some suggestions). It’s a reflection on where this process can go wrong. Specifically, my son’s questions reminded me of one my darkest hours as a people leader, and of the hidden challenges and crucial steps when it comes to onboarding new hires. It reminded me of the lessons I learned when I hired a brilliant woman that we’ll call Rose.

A friend of mine, JP, had hired me to lead a sales operations team at a fast-growing start-up. My job was to help build all the things needed to enable the sales team to scale. All of them. My head spun, constantly, with the mountain of tasks the team had to tackle. One of the biggest was hiring. To achieve our goals, we needed to hire A LOT of salespeople. And once we hired them, we needed to train them, quickly, so they could get into the field and be productive. I knew from past experience that effective training and enablement isn’t something that can be done off the side of your desk. I needed to find a pro, and fast. One of the first items on my very long to-do list became: Hire a sales enablement leader.

Enter Rose.

She had been referred by a trusted colleague who described her as an “enablement rockstar." When we met, I knew instantly that I had found my enablement leader, and I was thrilled when she accepted our offer. I began preparing for Rose’s first day.

Enter the list.

I began creating a list of all the tasks that Rose and I could get started on. Our first sales academy had been scheduled and was only weeks away. We were quickly adapting our pitch and product messaging. There was so much to consume. My list was going to help Rose feel organized. I was going to be there by her side to help her work through it. I would be her partner, her collaborator. It was going to be awesome. I congratulated myself for being so organized and for thinking of what it would take to help Rose get started.

Rose’s first day came. She showed up on Monday, on time, with a huge smile and the infectious energy that had won me over during the interview. I met her at the door and walked her through the requisite start-up loft, to the company kitchen with the standard cold-brew coffee, 16 types of cereal in transparent dispensers, unlimited hummus, pop, beer, Clif bars, and countless other goodies to keep the team fueled and working hard. Rose and I sat down. I got her a coffee. I quietly congratulated myself on being a great manager.

I brought out the list.

For the next hour, I explained the items on the list. Rose was engaged. She asked lots of questions. GREAT questions. Only an hour in and she was already adding value. This was amazing. What a great hire. We left the meeting with a new list of tasks for Rose. After a few introductions, making sure she got her computer, etc, I ‘set her free’ to do her thing.  I would be there if she needed anything. All she needed to do was ask.

The week went by in a flurry of activity. I checked in periodically on Rose, but I knew that we had ourselves a rockstar, so I mostly left her to her own devices. She’d tell me what she needed. On Thursday, JP, my boss, aka VP Sales, aka friend, asked me to go out for a coffee with him. “What about the cold brew on tap in the kitchen?” I asked.

“No.” he said. “Let’s get out of the office.”

Something was up. Executive shake-up? Were we being acquired? New round of funding? What clandestine start-uppy thing could this be about? 

We got our coffees. “Rose is going to quit,” he said.

“What?” I gasped. I felt the blood drain from my face. I was stunned. “Why?” I stammered.

“She’s overwhelmed,” he said. “She walks in every day dreading it. What did you do?”

What did I do!? I had a list! We talked and shared. I got her a coffee. I told her I was there for her. I was a great manager. This couldn’t be right.

But it was. And I wasn’t.

I can’t remember exactly how the rest of the conversation went. I do remember being wildly embarrassed and feeling horrible about how I had made Rose feel. I also remember coming to the realization that I had been so fixated on helping Rose to become productive that I totally forgot to welcome her, to recognize that this was a big change for her, and that that change would need to be managed to make her feel safe. I had waited for her to ask me questions, but I hadn’t asked any of her. And now here I was about to lose a rockstar less than five days after she started. Devastating.

The next morning, I asked Rose if she would meet with me. I got her a coffee. I had no list. I apologized with every ounce of sincerity I could find. I had no excuses. I asked her if she would consider starting over. I asked her to collaborate with me on a new list of what she thought she needed to get started. She had thoughtful, insightful ideas.  I was far from perfect, but my approach had changed. This time I had the person and not the productivity as the priority. Make no mistake, Rose wanted to be productive, but she needed to be welcomed. She needed help in managing the change that comes with a career move. She needed to know that the person assigned as her leader was watching out for her first. Or, at least, be shown a little empathy.

Empathy - maybe that is the core of it. After all, there are few things we can’t be effective at when we start from a place of empathy.

Thankfully, Rose agreed to give it (me) another shot. She went on to be one of the greatest assets the sales organization had. The programs that she developed and led were nothing short of world-class. She is now a sales enablement thought leader and continues to inspire professionals. To think that how close we were to losing her.

As an aside, I keep another list, of the top people I’ve worked with over the last 25 years, that I would hire should I ever decide to start my own company. She sits firmly in the top 5.

As I prepare for my new gig, I’m excited, inspired and a bit nervous. Like my son said, “New teachers, new friends, new classes.” And I'm reminded of Rose, of the importance of the relationship between a new hire and their direct people leader. That relationship will strongly influence a new employee’s impact and performance — and so it’s important to get it right. While every day can be full of moments that matter for the people we lead, I challenge everyone involved in onboarding make those first few days an exceptional experience. It can help to set the tone for years to come.

Please share your thoughts and ideas. I'd love to learn 'tips and tricks' for having an incredible impact in those critical first few weeks.