If you need things to change at work, you may need to have several awkward conversations.  They fall into 3 main categories:

• Conversations at work
  To make the changes you would love to see happen, you may need to make some requests or suggestions to your boss or your co-workers. There are ways to do this that will have a greater chance of a positive result than others!
• Conversations at home
  We shouldn’t pretend that asking for change at work is without risk. And you certainly can’t assume you will get everything you ask for. That means before you risk your livelihood, it’s probably a good idea to share your plans with your loved ones.
• Conversations with yourself
  This is one that often gets forgotten: you may need to change yourself too. Even if your dissatisfaction with your work is completely reasonable, making it better may mean changing your approach. Hence, that awkward conversation with yourself – often the one people avoid most!

Let’s look at each in a little more detail.

A conversation with the boss

Making your work more enjoyable usually means changing one three things: the things you do, the things others do for you, and the way you are treated. Most of these are, at the least, influenced by your boss. And how you ask your boss will make a huge difference to how willing they are to accommodate you.

In his excellent book The Magic of Thinking Big, David Schwartz introduces the concept of ‘making yourself easier to lift’. Essentially, this means making sure that you identify how your boss helping you will also help them. Consider which is going to go down best, “Boss, I need you to help me!”, or “I’ve got an idea that can help you, lovely Boss.”

It’s important that you don’t come across as needy and whiny, with only your own interests at heart. While it’s generally accepted (by decent managers, at least) that happy workers do better work, “Make me happy or my work will be shit” is perhaps not the most persuasive of arguments!

So find ways to show how the changes you’re proposing are going to be good for the whole business. And ideally how they will make it easier for your boss to achieve their objectives. And even get a bigger bonus!

(but please don’t fall into the trap of thinking the boss is all about the money, I’ll be exploring that in later posts)

Awkward conversations with colleagues

Some changes don’t even need the boss to OK them. Maybe you just need co-workers to support you in a different way. If you can agree better approach between you, your boss will likely be delighted not to get dragged into it all.

Once again, you can’t make it all about you. Be ready to show how the changes you would love will also be great for others. Observe what they love doing, and what they hate. Find out what gets them excited. That’s going to mean getting to know them, at a deeper level than their job role and performance.

And the funny thing is, getting to know each other better will probably make the workplace a more pleasant place. It will certainly stop any assumptions that are being made, on both sides, about what’s behind certain behaviours. It will even give you the opportunity to actively do things that make work nicer for your team-mates.

And people are far more likely to help you, if you’ve already helped them. Cialdini’s reciprocity principle of influence; getting what you want means influencing others.

Conversations with loved ones

Before you have the awkward conversations at work, you’re going to need to speak to the people who could be affected if it all goes wrong. Because it might. Putting your head above the parapet and saying you’d love change can be risky.

If your boss can’t (or won’t) accommodate what you need, you could be faced with the choice to knuckle down or leave. If your boss doesn’t like the way you ask, that might even precipitate a departure that isn’t by your own choice.  Those who rely on you deserve to have been prepared for any unfortunate result of getting it wrong.

In an ideal world, your family wouldn’t want you to have to just put up with something that makes you unhappy. But very few of us live in an ideal world. We live in a world of mortgages and bills, of school fees and expensive birthday presents, of holidays and hobbies. Of a necessary income level, and where jeopardising all that is a matter for discussion and planning.

You will need to let your loved ones know that you’re looking for change. They need to know that you’re not happy, and to what extent. That may require a level of honesty with each other that’s been forgotten in the bustle of home improvement and parent-teacher meetings.

You can probably be a little more selfish in your conversations at home than you can at work. Your happiness likely matters to your family; certainly more than it does to your work-mates. But you still need to show the family how making these changes will make their life better. Even if it all goes pear-shaped, and you end up looking for another job.

 So take the time to understand any fears they have. Respect their ‘red lines’ they would be unhappy crossing. Together, come up with a plan to put things right if the worst were to happen. Draw on the strength of the domestic team; possibly re-energising it in the process.

Awkward conversations with yourself

True self-knowledge is essential to happiness at work. If you don’t know what you truly want, getting it risks being a series of lurches away from what you don’t want. You may get lucky and manage to resolve each issue, but still not find real fulfilment.

You need to get beyond the day-to-day niggles and irritations. Dive deep into what you are really looking for from your working life, at a beingness level. Get beyond what you want to do, into who you need to be.

There are myriad ways to achieve this level of self-awareness, and I’ll be discussing my favourites elsewhere in my work. For the purposes of this post, just be aware that although I’ve put this conversation with yourself last in my list, it’s the most important, and the one you need to have first.

If you’re lucky, there will be someone in your life with whom you can start the exploration. A partner, perhaps, or a parent, or sibling. Possibly a great friend.

Many people prefer to be a little clearer yourself before sharing your uncertainties with those close to you. If that’s you I’d recommend you find yourself a good coach. Or if you’re part of a spiritual community, maybe talk to your leaders or elders.

Whatever works for you, do it.

And please, do it before you speak to the boss.

More about awkward conversations

In future posts I’ll be exploring some tips and techniques for each of these types of potentially awkward conversations. 

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