Lessons from my boss #1

In a number of organisations, there's a practice of appointing a "staff assistant" to the CEO or other senior leader, where the intent is to provide exposure and development opportunities for the staff assistant, while hopefully being useful to the senior leader. 

Examples in the Government include the role of Principal Private Secretary to the Prime Minister or senior cabinet leaders, or possibly the Justice's Law Clerks for the High Court judges. In the private sector, titles include staff assistant, and for more senior appointments, even Chief of Staff.

Many years ago, I was working late in the office when I returned to my desk from a meeting. Some of the office lights had already been turned off, so it was a bit dim, and the office was quiet. When I got to my desk, I saw my boss' boss sitting in my chair! I half thought to myself - oh no. I'm gonna be fired.

I wasn't fired. Phew. But she *was* asking me to leave. She asked me how I was, and then in characteristic style, quickly jumped to the meat of the matter - she'd like me to move out of the legal team and be the staff assistant to the CEO. 

I had been a lawyer all my life to that point. I had only moved to this industry as an in-house lawyer a year ago, and I felt I knew very little about the business. I had deep reservations about moving away from the law, and doing something I had no idea how to do. Worse, I would expose my ignorance to the CEO himself. 

But with a bit of chip on my shoulder after leaving my previous job, I had told myself, whatever they ask me to try in this new place, I'll try. So I said yes.

It turned out to be one of the best decisions of my work life. I'm not sure if I can pen them all in one blog entry, but here are just a few of the long-lasting life lessons I learned from my stint as staff assistant all those years ago.

You're here to learn

One of the first things the CEO did was to puncture my ego. He asked me what I thought I could do for him, and I said, well, I can advise you on legal and regulatory issues, and my bread and butter is writing, so I can write your speeches. Then he asked what I was not good at, and I said, oh I'm not so good at numbers, so I can't do that.

At which point he immediately made my first task to work with the Head of Finance on the quarterly numbers!

I asked him why would he want to make me do something I just told him I couldn't do well. And he replied, please don't be mistaken that you can be useful to me, even on the things you think you're good at. You're not. You're here to learn. Now go learn the thing you don't know.

Oof. That was deflating. And perhaps his approach might not work in the present, gentler age we live in today.

But looking back, I now know of course, that he didn't mean it literally. Of course he wanted me to be useful, and of course he had expectations of me. But the point is that he was more intent on helping me, than for me to help him. So he sent me to do something he knew I had to learn, rather than something I already thought I knew I could help him with. Amazing.

The takeaway: as leaders, we should strive to make it safe for our people to learn, be generous about helping them to grow, and be willing to tolerate some sub-optimality so that they can fulfil their potential and grow into the people they can be. 

Your opinion matters

On a day to day basis, I would sit in his meetings with other senior people in and outside the company. He even made all his emails accessible to me, so I would literally see all his mails in a completely transparent way.

As you might imagine, I was very quiet in those meetings, because I thought I was in way over my head. But after these meetings, he would often ask me what I thought. I recall that there was a particular acquisition that we were considering, and senior management had proposed going ahead. After the meeting, he asked me, in front of the senior manager who was proposing it, whether I thought we should go ahead.

I gulped, and then thought, ah well, in for a penny, in for a pound. So I said no, I don't see how this acquisition will lead to anything useful other than itself. It didn't seem like a bridgehead to anywhere.

I'd like to say he agreed, we pulled the plug, and I was right. The opposite happened :D He said, no I think you're mistaken, and explained why. We went ahead, and eventually I was proven wrong.

But he had a way of disagreeing that made me feel that my opinion mattered to him. Over the course of my time as staff assistant, there were a number of other occasions where he was going to do something, I disagreed, and he decided I was right.

I distinctly remember one particularly sensitive situation where he was on the verge of bringing in a very senior person as a new hire. When he asked me what I thought, I said, I don't think so and explained why. And he actually pulled out of the hire! 

That was really freaky to me as a young officer, and I came away from it thinking - he is actually listening to my opinion! And it made me ensure that my opinions in future were well researched, and well thought through.

The takeaway: as leaders, pro-actively ask for your people's opinions, including the contrary ones and the junior ones. When people believe that their opinions matter, they will go above and beyond to form robust opinions, open their mouths and move their hands and legs to help you.

You're here to solve my problems

Some time into my term as staff assistant, he asked me to get something done with one of the senior leaders. I went to that person, explained what needed to be done, and was roundly declined and kicked out. I tried again, but got rejected again.

So I thought, I guess I better tell my boss. So I went into his office to bring the bad news.

His desk used to be setup in such a way that his computer was off on the side, so if he was on the computer, he wouldn't be facing you. As I explained the situation to him, he continued typing, not even giving me eye contact.

And after my extremely persuasive (ha!) explanation, he continued typing for an uncomfortable period of silence. 

Now what? Do I leave the room? Is this meeting over? I dunno. So I kept sitting there.

Finally, without stopping his typing, he said, [my name], I pay you to solve my problems, not for me to solve your problems.

More silence.

At this point, I realised the meeting was now indeed over :D

So I left his office and headed right back to that senior leader's office to get the job done. And this time, that leader agreed. Why?

Because I now knew that I had no backstop. My boss was not going to come to my rescue. I had to get it done. So I became more insistent, better argued and persuasive, and oh, I don't know what else. The bottom line is, what I thought I needed my boss to push through, I could actually push through myself.

I now say this to many of my own team, albeit in a much more 2020s-appropriate tone :D But essentially - [X], we pay you to solve our problems, not for us to solve your problems!

The takeaway: don't let your people get away with making their problems your problems. Look, sometimes it might be unavoidable, and you could probably do it quicker and better, but don't succumb to the temptation of fixing it for them. It's not good for them. Make your problems their problems - it's an opportunity to learn and grow, and they deserve that opportunity.

People matter

As staff assistant, I would work with the CEO's secretary to arrange his schedule. A CEO's schedule is typically packed from morning to night, so getting into the queue can be tricky.

I would often see 1-1 catchups scattered all over his calendar, and I once asked him, can't we just cancel some of these 1-1s? You don't even have an agenda for these catchups. But he very rarely cancelled. He genuinely thought that it was important to spend time with people, even without an agenda, to know not just *what* they were doing, but *how* they were doing - by which I don't mean how they're doing the what, but literally how life is going.

And these 1-1s weren't confined to his own reports. He'd get seemingly random mid-level execs, and junior people like myself and even fresh graduates to come in and spend time to just talk.

I think this built a culture that "people matter", and motivated people to go above and beyond. And it's this sort of thing that enables him to this very day, years and years after he's left the place, to still gather a huge bunch of ex-colleagues, junior and senior, young and old, to gather to meet, just because. 

Not every leader needs to adopt the same approach - there are many different leadership styles, and many of them are just as effective. But I point this out as one which does work, and seems an enjoyable way to work.

The takeaway: make time for people, and not just on what they are doing. When we know we matter beyond what we do, we build loyalty, trust and togetherness. If nothing else (and in my view, it is not nothing else!), it makes for a positive, enjoyable work experience.

As I suspected, there's not enough room in one blog to write about it all! But I'm glad I had the chance to live through it all and apply some of it in my own life. And if I'm lucky, perhaps someone else will have learned a small bit of what I learned from my boss!

"Therefore encourage each other and build each other up, just as in fact you are doing." 1 Thessalonians 5:11

"In humility, value other above yourselves, not looking to your own interests but each of you to the interests of the others." Philippians 2:3-4

"And let us consider how we may spur each other on to love and good deeds." Hebrews 10:24