How to Train Your Boss and Become a Trusted Advisor at Work

Welcome to the Elephant in the Boardroom, where we talk about the business practices we love. Love to hate, that is.

These are the practices that frustrate employees, anger customers, and hurt shareholders.

I'm Terri Long.

And I'm Jeremy Eaton.

And we are the co-CEOs of Harvest Earnings.

We challenge conventional wisdom, share our stories, and give you advice you can use at work, and even sometimes at home.

It's time to banish those elephants in the boardroom.

Okay, so today we are going to talk about how to train your boss.

Which, of course, makes me think of how to train your dragon.

But more specifically, we're going to talk about how to train your boss to make you their consigliere.

Now, we struggle with that terminology because, of course, it's about being a trusted advisor to the mafia don.

I don't know, is that the right?

So we probably don't want to use consigliere.

And we also kind of think of it as managing up.

But we don't necessarily want to use the term managing up because that's considered negative.

That's like you're doing that for your own gain and you're just sort of faking it.

So how to train your boss so that they make you their trusted advisor.

And that should be good for you, obviously, but also be good for the company, assuming you're a good trusted advisor.

We've seen quite a few really great trusted advisors through the years.

Ted Smith at Heinz comes to mind.

Tim Schack at PNC.

I think we've talked about Tim before.

He's amazing.

Our good friend Nancy Kruseger at Manpower was a trusted advisor to Mike Van Handel, who was their CFO.

Yvonne Truppiano at Spartan Nash was very much trusted advisor to Dave Staples.

I mean, we could go on and on.

So forgive us clients if we haven't named you.

So we're going to talk about how to gain the trust of your boss so that you become their trusted advisor.

As you said, this is all for the purpose of helping bosses be better, not just about your own personal career.

Well, it's both.

It's both, right.

Right. It's for everybody.

So the first thing.

But also, your boss being better just makes your life better.

And unfortunately, particularly because org charts are drawn where someone just is, their box is just higher than other boxes.

Everyone has this model that, you know, a boss is knows everything, should be doing everything.

They train the people below them.

We don't view it that way.

Most of what goes on in a company is very collaborative, and everyone is a little bit in a fog of battle, as it were, and need help from everywhere.

So the first thing is, and this is this is true of just human beings relating to human beings.

Give positive feedback.

Don't fake it.

Don't suck up.

This is about being judicious in giving clear, specific, positive feedback.

So, for example, when we hold our initial steering committee, we tell people ahead of time there might be a tendency when they hear something to react very negatively.

But if they do, they're never going to hear the truth.

For example, for example, when somebody came in and presented that they an idea to stop a program that existed, the CEO had thought that program had ended years ago.

Yes.

Could make one angry.

And he was very angry.

But up till that point, he had been very good at just listening and encouraging and getting the truth.

After the first steering committee, it is almost always the case that people will ask us, so how did we do?

And if we say, well, you did this thing not so great, this thing not so great, this thing not so great, we're not going to be listened to.

So there's almost always a way to formulate, well, what was the positive thing and dwell on that as the model to be replicated.

So we will say to people, you did a great job, you know, not reacting and getting all this information and that's going to spread through the company.

You're going to get even more of that.

So finding those nuggets of positivity, not always nuggets, maybe swaths and using that as the thing to accentuate the positive as the song requires us.

Oh, boy.

So we didn't, for example, say to the person who napped at one point at one client during the steering committee that good job not startling too much when you woke up.

And so lest everyone think we are only saying give positive feedback because we absolutely don't mean that.

We have the expression give the cold cup of coffee because we often there's an expression.

I don't think we made this up, but the boss never gets the whole truth or a cold cup of coffee, meaning, you know, they're fed.

They're fed sort of what people want them to hear and they're coddled to.

So that's why not the cold cup of coffee.

But a boss can't do their job well if they don't get the whole truth, including the negative stuff.

So we do give constructive feedback when it's warranted and we appreciate it very much from our own people as well.

And so, you know, an example from my banking days, we had a big loan going south and I, as unpleasant as it was, I made sure to tell my boss what was happening.

Every step of the way, because the last thing I made, it would have been even worse for me to go in and say, surprise, that loan you thought was all good.

Oh, it's gone south completely.

Now you've got to give the cold cup of coffee along with the positive.

And another example that somebody told us, someone who worked for us years ago knew that someone else in the company was stealing from the company.

And, you know, hard, hard thing to express, because everybody liked this guy.

But she came and she told us, heads up, this is what I believe is happening.

And she was right. But hard, hard to express.

But she did it. And that helped us.

And she was pretty junior. And if we had done nothing or just tossed it off, and now she had to continue to work with this person knowing that it might come back to haunt her, you know, it took some courage.

But we also gained a huge amount of trust in her and respect of her that she did this.

And we did act appropriately. Yeah.

Okay. Should I do the next one? Please.

We always assume or often assume that our bosses are going to know how our job works, or at least how the people who work for them, how their jobs work.

Then when we're working for them, it's like, oh, my God, they just don't really understand all the challenges and difficulties and nuances and what I need to do a better job.

So it's very important that you proactively, in effect, teach your boss about your job so that they are better positioned to make good decisions, to be empathetic, to know what you're going through.

And, you know, that doesn't mean an hour-long lecture during an hour-long staff meeting.

But there's often openings to say not just, well, it'd be nice to, you know, if we could fund X, but to explain a little bit about what is going on so that they understand why, oh, funding X would be a really great idea.

And this is, of course, especially important if your boss hasn't come up through, you know, your team or your department, whatever, hasn't had your role in the past.

I'll throw in one little extra. We've talked about this undoubtedly before, but we say no TLAs, no three-letter acronyms, because even though your boss is your boss, they may not know every TLA that you use.

And it's awkward sometimes for people to ask. Everybody should feel free to say, I don't know what that means, but a lot of people aren't.

And to this point, you make about if your boss hasn't had your position, the higher up you go in the chain, the fewer of the positions that report to that person, they will have had personal experience with.

And by the time you get to the CEO, they do not have personal experience with 300 different functions that are going on in the company.

And even the ones they have had exposure to or had done in the past, they may have changed completely by the time the CEO had since the CEO had had it.

OK, so the next one's hard for the first part's hard for a lot of people, and that is to praise yourself.

The second part is to praise your coworkers. That comes more naturally to many people. Praising yourself is hard.

You know, we're told not to toot our own horn. It's important for the boss to know everything.

Not, of course, just the cold cup of coffee, but the good stuff so that when they are talking to their boss or the board or whoever they report to, they have that information, even if it's small.

But giving them that fodder to talk about is hugely helpful to them. And it's hugely helpful to you.

I mean, for for example, at Google, I understand you're forced to toot your own horn, at least as part of the promotion process.

You have to say here are the good things I've done and here are the people I've helped.

And so, you know, keeping your bosses apprised of that along the way is just a good a good thing.

And your coworkers, obviously, that's that's all part of it, too.

And you'll be beloved. Also, if you say, you know what Bob did today, he did this really great thing. And so did Jane.

So the next one is take initiative. Now, this seems so obvious.

But as they say, when you're up to your neck in alligators, you know, it may just seem a little hard to take initiative on things.

I have never been in that position. No, no, thankfully.

The funny thing, of course, is there's a contrary phrase, which is if you want something done, ask a busy person to do it.

So if taking initiative is, you know, I once spent a Christmas vacation organizing essentially every document of a of a process that had many,

many different documents and phases, things, elements to it into coherent, consistent templates and binders so that the entire team would literally be on the same page.

Nobody had thought to do this before because we're all running around doing this stuff and my boss hadn't asked me for it.

But it was very much appreciated and showed her that, you know, I was I was thinking about how do we build the firm and make it better?

My good example of this that certainly made ended up making a huge difference in my life, really, I believe, is that a hundred years ago, I offered to be the C.R.A.

officer of the bank I was at.

So for those who don't know what that means, it's the Community of Reinvestment Act.

And back then, in particular, it was that they hammer if you did not do well at community reinvesting in your community, which was well defined.

You could be prevented from buying other banks, which this was in absolutely high growth mode.

And so it would have been devastating.

And we were in a we were in a rough position.

We were in a downtown area without a lot of residential to lend to, which was a very important part of the Community Reinvestment Act.

But the the woman who was playing that role left the bank.

It wasn't it was an extra thing to do.

It wasn't a full time position at this bank.

And it wasn't a lot of fun.

And we were facing what was clearly going to be an exam soon.

And so I raised my hand and told the president of the bank that I would take this role.

And I am sure that went a very, very long way for him to appreciate me well.

And I, of course, then busted my butt and we passed that exam.

That was a huge relief to him.

I mean, I think the offering solutions is very similar, really, to taking taking initiative.

It's you take initiative is sort of goes hand in hand.

In my case, offering to be CRM officer was a solution to Mike because he needed somebody to play that role.

I mean, one thing is that the higher up people go on the chain, the higher the percentage of their day is faced with people posing problems to them

and wanting them to come up with solutions to often intractable or really challenging problems.

So, for example, there was a leader, a recent client had a call center, among many other functions.

And to improve that, they really needed a AI system that unfortunately required new telephony.

And that new telephony would require the whole company changing their telephony to make the numbers work.

And that would cost a fortune. So that was not acceptable.

Or you could keep going with the old system, which led to bad customer service.

Well, you know, not as high customer service as they'd like.

That was unacceptable. So you have this well-meaning but intractable problem that everyone was kind of gnashing their teeth at.

And this guy just said, well, I'm going to go with half a loaf.

I'm going to figure out how to use humans, people to do some portion of what the idea.

And he presented this solution and everyone went, right.

But, you know, it's not Nirvana, but it moves us forward and isn't making the CIO and the CEO have to figure out a problem that really could not have been figured out anyway.

And AI versus human, AI artificial versus human intelligence is going to be a subject of a podcast very, very soon.

Yes, it will. That world is rapidly changing, obviously, and our connection to it is as well.

Spoiler. OK, so the next one is for the bosses who aren't good at clarity, which is most.

I mean, because most people aren't good at clarity. Right. Help them out.

Why don't you say the communication quote?

Oh, the single biggest problem with communication is the illusion that it has occurred.

It's one of our all time favorite quotes, which admittedly is a long list of all time favorite quotes.

But that is that is actually right up there because it happens constantly.

Right. You think you've sent something and it's clear, but it turns out later.

No, not even close. So help.

So if you're in a meeting, for example, and and particularly if the boss is talking, I mean, this happened with us one time.

You were doing the talking. I'm doing the observing.

I notice. Bill Demcheck, now CEO of PNC, then CFO, clearly from a reaction misinterpreted something you said,

and I was able to then clarify it because, you know, I was I was doing the watching.

So when you're talking, it is actually harder to make sure, you know, that you're perusing the room and seeing that everybody is on board.

So if you can help by maybe reiterating, say, you know, hey, boss, this is what I understood.

You say, can I summarize this? Is that right?

And, you know, ask the questions if you're not clear, because probably everybody else in the room isn't clear as well.

You are the king of this so much sometimes that I do have to say, Jeremy, we overstand and make you stop.

But it is just like built into your DNA.

You are the king of explanation, which mostly I appreciate occasionally.

Not so much. I I understand.

OK, yeah. And often people speak unclearly because, in fact, in their own mind, they don't realize there's ambiguities that they don't know about,

haven't thought about, don't know what the answer is, and they use something ambiguous.

And to have someone say, well, we could do it this way or that way.

What do you think makes them go? Oh, yeah. Right. OK. Good point.

Well, I mean, the phrase you used was you can't get this wrong.

And the English language, there it's there are so many words that mean the opposite.

You know, the one word can mean this and then the absolute opposite of this, depending on the context.

It's craziness. I'm sure there's a word for what that word is, but I don't I don't know it.

But you can't get this wrong. You just meant there was no wrong answer.

But he heard it as, oh, my God, it's super important that you do not get this wrong.

Complete opposites. Well, the New York Times just had a headline that said Democrats can't wait to midterms.

Does that mean they're they're so anxious they can't wait for it to happen?

Or does that mean we can't wait that long? We've got to do something now.

I don't know. And that's the New York Times.

Yeah, that's pretty amazing. I'm going to assume it was the latter, not the former.

I mean, but it's both. I mean, or maybe it's both.

Maybe they actually thought they were being cute. I don't know. I don't know.

But it is no shame to be unclear. We all are a lot of the time.

What is a shame is to let it ride and not help the person clarify when it's important.

And and they will then begin to turn to you to like, did that make sense?

Kind of. So our last.

Well, I guess we have two more. The next one is understanding their priorities and offer help when they're under pressure.

So you like to say, oh, everybody assumes the boss has got things under control and has resources at their disposal.

But that's that's not always the case. No, they're treading water also.

So I'm going to I'm going to tell a mash story, but I'm going to wrap it with the last one, which is show them that you care because it is lonely at the top.

Even if your boss isn't the top, but it is it can sometimes feel lonely being a manager.

So my mash reference, for those of you who are mash fans, is a very important episode for Major Margaret Hotlips Houlahan.

And Loretta Switt, I think, said this was her favorite episode of the 11 seasons of mash or 12.

I can't believe I don't know. But it's one of those. She has been very hard on her nurses, one in particular.

She's a newlywed and her husband has got some leave.

He's in the army and her husband has some leave and the nurses conspire to get her some time off.

But Margaret is mad, doesn't let it happen. And anyway, it's very hard on them.

The nurses hang out together a lot. They make coffee, they gab, they whatever.

And Hotlip Hotlips, Margaret Houlahan is not invited.

And she finally sort of expresses to them that this hurt her a lot and that what her motivation was, of course, you know, she's a major in the army.

She cared very much about her job. She wanted to make sure that protocols were followed and efficiency was maximum and that, you know, the most lives were safe.

So she had very good goals and objectives and a reason to behave the way she did, but was still human and was very hurt.

And so she finally says to them, you never even offered me a lousy cup of coffee.

And they sort of realize, oh, showing her that they cared about her and understood her would have been a very useful thing for the unit.

And then they finally do. They invite her for a lousy cup of coffee.

And that is the phrase that she uses that they say, would you like a lousy cup of coffee? Great show.

And in in our everyday workplace, that might translate even into something like, you know, your boss has this big speech that has to suddenly get written.

And you just pop your head and go, you know, can I help with the speech or whatever it is?

You know, so you're you're aware of the pressures they're under and are offering to help.

Maybe the answer is no, but the offer will not be forgotten.

Yeah, absolutely. And you will become their trusted adviser.

Should I do a very quick recap? Yes. One, give positive feedback to give the cold cup of coffee.

So negative feedback, but also negative information that's not necessarily feedback.

And it's fact based and nonjudgmental, fact based and nonjudgmental.

Train your boss. If your boss doesn't know your role well, help them understand that role.

Praise yourself and your coworkers. Take initiative.

That's an obvious one. Offer solutions closely related.

Help clarify your your boss's points or maybe even other people within your your team that helps your boss as well.

Understand their priorities and show them that you care. Excellent.

And then you win. And the boss wins and the company wins.

OK, on that back to back to work. Back to work. Cheers. Bye. Bye.

Thanks for listening. To learn how Harvest Earnings helps large companies overcome the bad practices,

visit our website HarvestEarnings.com or email us at info at HarvestEarnings.com.

Also, please subscribe wherever you get your podcasts.

And if you're feeling generous, leave us a rating and a review.

It really helps others discover the show. Until next time, I'm Terri Long.

And I'm Jeremy Eden. And now it's time for us to get back to work. Bye.