Your 5 Hardest Conversations

Episode #312 Your 5 Hardest Conversations

FROM THE PHILOSOPHICAL, TO THE DEEPLY PRACTICAL

Last week, I leaned into the more philosophical side of my content with my 12 hard leadership truths. This week, we’re back at the coalface with a really practical newsletter to help you nail the five hardest conversations that you’re likely to have to face as a leader.

I go way beyond my more general guidance on handling conflict, as I give you nuanced tips for nailing each of the five different types of hard conversation that you are going to face.

I start with some overarching principles, just to make sure we’re all on the same page, particularly if you’re fairly new to my content. Then, I dive right into the five hardest conversations. All of them are slightly different, so this could well be one of the most practically valuable newsletters that I’ve ever written.

THE FOUNDATIONS OF HARD CONVERSATIONS

What do you need to know before we start? I just want to run through five foundational concepts. These are separate from the five hard conversation types that we’re going to look at in a little while, but it’s just going to get us on the same page to make sure that we’re all speaking the same language.

1. If you need to have a hard conversation, don’t delay it.

There are some areas where procrastination can work out in your favor. Just occasionally, you’re going to be surprised when something you are procrastinating over gets solved – and of course you are delighted that you never had to do it after all. Happy days! This doesn’t happen very often, but when it does, it’s absolute gold.

Having said that, I am 100% convinced that conflict situations always get worse with the passage of time. You’ll avoid them… until you can’t, and then you’re really in trouble. The last of our five hard conversations is going to show you why.

2. Your brain is going to try to push you into rationalization.

Our primitive brain is there to protect us and keep us safe. It alerts us to danger by triggering our fight or flight response. We have to learn to move beyond that subconscious trigger.

We can’t stop it from happening, of course, because it exists at the instinctive DNA level – it’s one of our most basic functions. But we can learn to feel the fear, put it aside and move forward.

If you want to do this, of course, you have to learn to push yourself, and the only way to get more comfortable is by doing the reps. Repetition gives you skill and confidence.

3. Hard conversations are 90% will and 10% skill.

This is a perfect segue from the previous point. You have to break through the psychological and emotional barriers that hold you back. If you develop the will to step into the conversations, the skill will come. Of course, the skill comes with the reps.

Just make sure you’re prepared for the process. You have to expect to be bad at first. I was – everyone is! But I promise you, you will get better, and you will become more comfortable sitting in that tension.

4. Preparation is everything.

If you don’t prepare yourself properly, the conversation is likely to go poorly, so give every conversation the respect it deserves. If you learn to prepare properly, you’re going to be rewarded in multiples.

The beauty of this is that, as you become more comfortable, the time it takes you to prepare gets shorter and shorter. I got to the stage eventually where I was able to make an observation to myself, and then dive straight into a conversation with the individual involved while it was still timely, relevant and useful. I cannot tell you how valuable that skill actually is.

5. Conflict is an essential part of any leadership role.

Your success and happiness depend on it. When you’re leading other people, conflict is everywhere you turn – you simply can’t avoid it.

But I’ve seen so many leaders over the years, at surprisingly senior levels, still trying to negotiate the inevitable. My observation is that they are not happy people. They might be making a sh!t ton of money, but they have an incredible insecurity and tension around them.

You can’t avoid conflict, so just embrace it… and try to be kind to the bad leaders above you, too. They probably just never learned how to get a handle on conflict.

If you weren’t nodding your head furiously in agreement when I ran through those points, you may need to get more information on those basics.

I’ve dealt with these topics in numerous podcast episodes, so I’m going to refer you to just a couple of those if you want to bone up on them:

• Ep.206: It’s Still Respect Before Popularity
• Ep.6: The Psychology of Feedback, and
• Ep. 22: Feedback Made Easy.

Of course, if you really want to become expert in conflict situations, we dedicate a whole module to this in our online program, Leadership Beyond the Theory. Our only public cohort for 2024 kicks off in just a few weeks, so if you want to get an exponential uplift in your capability and confidence, this is where you’re going to find it.

HARD CONVERSATION #1: NEGOTIATING YOUR ROLE AND SALARY PACKAGE

This is a conversation where preparation is absolutely critical and we get an endless stream of questions on this one.

In fact, we released an online course last year called Landing Your Dream Job. A key lesson in this course was knowing how to negotiate your new position and remuneration. So, I’m just going to give you the cliff notes version of this lesson.

The first thing is, don’t negotiate anything until after the company has offered you the job. If you didn’t already know this, I reckon this one rule of thumb is worth the price of admission alone for reading this newsletter.

I see people trying to negotiate bits and pieces during interviews and follow-up calls. You don’t want to ask anything of your new employer until you have maximum leverage. It’s an old negotiating principle. And that point – the point of maximum leverage – is when the company has just decided that they need you in the role; that you are the best candidate for the job.

The second thing about negotiating your role and salary package is, know the company you are joining. Make sure you understand how flexible they’re likely to be around remuneration. Be aware of industry norms.

For example, if you’re going into a job in investment banking, or consulting for one of the MBB firms, you’ll have a very different negotiation than you will if you’re accepting a role with a government agency.

The third thing about negotiating your role and salary package is, know your market value. This is going to give you confidence to be assertive in any negotiations that you undertake on salary. So, do a bit of research. There are many guides out there from reputable providers.

And make sure you pull both the fixed and the variable remuneration levers, if they’re applicable at your level.

The fourth thing about negotiating your job is, it’s not just about the money. You may be able to negotiate a range of benefits that aren’t related to your base salary, such as:

• Professional development courses, or
• Flexibility of work hours and location; or
• Bringing forward a performance and pay review to the end of your probationary period; or
• The opportunity to work on interesting projects.

And then, of course, you’ve got the financial levers of sign-on and retention bonuses.

There are some ‘watch-its’ around this one, clearly, but this just gives you a flavor for what you can do.

And finally, ‘understand the contractual traps for young players’. If you’re joining at a level where you’re covered by a whole of workforce industrial agreement, then you won’t have a lot of flexibility.

But if you’re signing an individual common law contract, there are two things in particular that I always look at really closely: these are the termination clauses and the non-compete clauses.

I know when you’re just about to start a new job, this is the last thing on your mind. But it’s much harder to negotiate these later, so make sure you know the circumstances under which you can quit, and those under which the company can let you go.

Look at your notice periods and make sure you understand termination for convenience versus termination for cause.

These conversations are pretty difficult, but quite important to make sure you extract fair value and manage the risk of your new job, at the point where your negotiating leverage is at its highest.

HARD CONVERSATION #2: GIVING A DIRECT REPORT FEEDBACK 

This is really the primary forum for you to overcome your conflict aversion. Giving feedback to one of your direct reports can be really difficult. We’ve already spoken about the reptile brain and rationalization, which is why when you’re trying to avoid one of these conversations, you’ll be able to construct a thousand compelling reasons… all of which are completely irrelevant.

Then of course, there’s a fact that no one knows. Only you know – you’re the only person who really knows which conversations are required, so it’s easy for you to delay and to rationalize or to prioritize a hard conversation below your other busy work.

No one’s watching you if you decide not to have the conversation that you know deep down you need to have. Learning to step into these conversations, without hesitation, is going to create a competency and a mindset that flows through all other hard conversations, in any area of your work and your life.

This is the forum where you get to tame the dragon.

I’ve already given you a few podcast episodes to listen to that are going to help you with this, but I just want to make a couple of points.

 The best tip I can give you for overcoming your fear of feedback is: get out of your own head.

Your self-talk is going to be leading you to think only of the impact that a conversation might have on you, so you focus on your fear, your apprehension, and your discomfort.

Flipping the script gives you a totally different perspective, but to do this, you’ve got to really care about your people. You have to put their well-being and growth ahead of your own fear and discomfort. Not many leaders learn to do this willingly, without question or hesitation.

Instead of focusing on your fear of a hard conversation, you need to focus on one question:

“What does this person need to hear right now? What could I tell them to improve their chances of being successful, not just in this role, but in all their future roles?”

Well, that’s actually two questions, but you get the gist, right?

One of your rationalizations is probably that you don’t want to upset this individual or demotivate them. But that’s actually about you, not them.

The only other guidance I’d give is to start with baby steps. Start by having conversations about non-work and non-performance related things. Just develop a dialogue and get used to a flow of conversation. Once you’ve got a free-flowing leadership dialogue, it takes away one of the big impediments – the lack of connected relationship you have with your direct reports.

Once you’ve done that, everything gets easier, and you can broaden the conversation to cover all areas of work performance.

HARD CONVERSATION #3: GIVING YOUR BOSS FEEDBACK

We’re now in the realms of real nuance. Giving your boss unsolicited feedback can be really tricky. Even when your boss actively solicits feedback, it can still be tricky.

Often when your boss says, “Do you have any feedback for me?”, the expectation is that the feedback should be positive. Here’s a couple of rules of thumb that might help.

The first thing is, make sure you know what your boss thinks of you. How does your boss rate your performance? If you aren’t pretty confident that you have the trust and respect of your boss, you’re treading on thin ice. Why should anyone take criticism from someone whom they wouldn’t ask for advice?

Second rule of thumb, always ask for permission before offering feedback to your boss. Even if you feel as though you have a good relationship, don’t take that for granted. It’s unlikely your boss is going to say “no” but, equally, you have to be able to read the play. When she says “yes”, is she genuinely open to feedback, or not?

The third rule of thumb is, be really clear in your own mind about the one point that you want to make. Don’t throw in the kitchen sink – just be clear about what your point is, why you are making it, and how things could be better for the team if that feedback were addressed.

Clarity is a premium here, so do your homework first and link the potential change to a higher value outcome, like increased productivity or greater line of sight to strategy.

And the fourth and final rule of thumb about giving your boss feedback is, don’t make it personal. Instead of saying, you this and you that, couch your feedback as observations.

For example, “I’ve noticed what happens when the conversation isn’t allowed to flow in our weekly performance meetings”, or “I saw a lot of confusion in the team after that town hall meeting”.

Of course, if your boss doesn’t accept feedback at all and you aren’t happy with the way he leads, you may need to seek out a new boss. Leaders are learners, so if your boss isn’t a learner, don’t expect that they’ll change: it is incredibly unlikely.

HARD CONVERSATION #4: DELIVERING BAD NEWS

There are going to be literally dozens of situations where you need to deliver bad news to your boss… to your customers… to the board… to your suppliers… and, of course, to your own team. These conversations can be either in a group setting or a one-on-one situation.

The only thing I’d add to what we’ve already covered is this: when you have to deliver bad news, it takes real strength. This starts with taking on accountability, whether it was your fault or not.

When you step into the accountability, you distinguish yourself as a courageous leader who’s willing to stand up in the face of adversity. Your people are going to know that they’re working for a strong leader.

It’s quite disarming for the audience that you’re delivering the bad news to. Just think about it – when something goes wrong and someone has to deliver some bad news, it has a very different tone depending on how they do it.

Many people make excuses. But you know me, excuses don’t cut it. It doesn’t matter what’s coming out of their mouth, all I can hear is, “The dog ate my homework”.

How different is it when you see someone step into the void of a big problem and say, “I own this, I’ve got control, and here’s what we’re doing to right the ship. But make no mistake, we will get things back on track, and here’s our plan”. Doesn’t that feel completely different from the litany of excuses?

My tip is, whenever you have to deliver a major piece of bad news, tell the story.

It doesn’t matter whether it’s your board or an investor briefing or a disgruntled customer. Tell the story like you’re telling it to a friend at a barbecue on a Saturday afternoon over a couple of beers. Be relaxed, open, and truthful, and have the story structured so that it makes sense.

Typically, the story would consist of half a dozen key elements:

• What went wrong?
• What was the root cause of the failure?
• Why didn’t you anticipate it?
• What’s the impact?
• How are you going to fix the issue and get back on track? And,
• What are you going to do to make sure it doesn’t happen again?

If you tell that story with frankness and humility, delivering bad news is much easier than you would’ve ever thought.

HARD CONVERSATION #5: LETTING SOMEONE GO

This is the one that leaders dread the most, and we’ve all avoided it at one time or another.

There are a thousand good reasons that you can use to convince yourself that you should keep someone who you know can’t do the job. I’m not going to go into those reasons here.

There’s only one compelling reason why you need to make the decision to let someone go, and of course I’m talking about outside of restructures and redundancies. It’s because they’re not doing the job they’re paid to do.

Forget all the good reasons that rationalization is pushing into your brain to make you feel more comfortable. Of all the senior people that I’ve let go over the years, I’d say probably 1/4 simply didn’t have the capability or skill to perform the role to the required standard. But 3/4 absolutely had the talent, skill, and capability, and for one reason or another, they made bad choices about how they wanted to behave and perform… and those choices have to come with consequences.

There’s no doubt that we have a clear obligation to give everyone an opportunity to thrive and grow in their role, but we also have to hold them accountable for the choices they make. If we don’t, it drags the whole team down and the culture collapses. Of course, you’re not going to see it collapse all at once, but you’ll wake up one day and realize that your team is mediocre, at best.

Remember, weak leaders lower the standard to meet the performance. Strong leaders lift the performance to meet the standard.

If you are entertaining any hopes of building a high-performing team, you have to be in the second camp. You have to be willing to lift the performance to meet the standard.

My golden rule for handling a termination conversation is that it shouldn’t come as a surprise to the individual involved. The only way to guarantee this is to have many, many conversations over the time when you’re coaching and guiding them about what’s required.

If you are giving every individual high-quality feedback… if you are spending time working with them on the specifics of their performance… if you are making it really clear where your expectations lie… if you’re making it crystal clear what the minimum acceptable standard is… then it won’t come as a surprise to someone who hasn’t met the mark despite your best efforts.

But, if you know deep down that you haven’t given the individual this type of attention and support, you’ll be reluctant to push the button. And you should be!

So, go back to conversation two from this episode – giving a direct report feedback – and work on that until you’re entirely confident in your ability to lead your people.

If you let someone go and you’ve done it the right way, you’ll be able to look yourself in the mirror the next morning and say, “I’m confident that I did everything I could have possibly done as a leader. I used all my skill and committed myself to try to help this individual to grow and thrive, but for whatever reason, they chose not to meet the standard that I’m setting for the team.”.

DO THE REPS!

Right, that’s the 5 hardest conversations you’ll face as a leader. Remember, everything you do as a leader has the potential for conflict. Hard conversations come with the territory, but you can’t expect to get any better unless you first work to get mastery over your emotional state, and then develop the skill you need to hold these hard conversations capably.

You simply need to do the reps – there’s no way around it. But if you value this work, and you take it as seriously as you take strategy and finance and marketing, it’s going to pay you back in multiples.