When your toughest conversations are with yourself

We’ve written a fair bit and worked with a lot of organizations around Essential Conversations — our workshop program that helps leaders have difficult conversations with others (employees, peers, suppliers, etc).

The program works well, has a lot of a-ha moments, and helps leaders figure out how to have the conversations they’ve been avoiding.

However, working one-on-one with so many leaders in our coaching programs, we’ve come to realize something else — with many successful leaders, the toughest conversations they’re having are with themselves.

I recently read an article in the Harvard Business Review1 that dove into this topic and it hit home. So many of our clients, who are themselves respected and sometimes revered senior leaders, are pounding themselves with criticism and self-doubt.

One leader we know excelled throughout his career — rising rapidly, taking on ever-increasing responsibility for people, budgets, product delivery and organizational reputation. His teams grew from a handful of people to a few dozen, then a few hundred, and later thousands.

He exuded confidence in decision making and vision setting, he gave speeches around the world to hundreds at a time, promoting his company’s product with great success.

And yet, on the inside the successes were celebrated fleetingly while he would layer-in things like “you should have seen that coming,” or “that talk was lousy, you didn’t hit the right notes when you needed to.”His team was committed to him and to the product, yet he would worry that he didn’t look “strong enough” or that they would know when he was struggling with a decision and would think him incapable or unqualified.

His team was committed to him and to the product, yet he would worry that he didn’t look “strong enough” or that they would know when he was struggling with a decision and would think him incapable or unqualified.

Another executive we work with is seen as one of the most innovative and dynamic thinkers in her field. She devises new ideas and innovative approaches that leave her team in awe. Yet, she’s so worried that her idea might be wrong or that there might be solid reasons for it not to work that she holds back most of her ideas. Or, she shares the idea and then tries to micro-manage their implementation, to prove it will work.

The team that is so often in awe, often ends up frustrated and exasperated. They see her creative strength but her own worries are diminishing her star power and losing the commitment of those around her.  Many of these great leaders acknowledge that they can have tough conversations with others because they have

Many of these great leaders acknowledge that they can have tough conversations with others because they have to, if they’re to ensure their culture is strong and their success aligned. I hear things like “tough on the problem, gentle on the person,” or “high expectations and high support,” and “I decide which battles are worth fighting — where do we want to ensure we learn from a mistake and where is it ok to just let it go?”

Yet, and I’ll bet you know where I’m going with this… these same folks rarely, if ever, apply those tests to their own self-talk.

When something goes wrong how often do you get tough on the issue, so it doesn’t happen again, while being gentle on yourself?

How often when you’ve set enormous expectations for yourself, do you also ensure you have enormous support? And of course, how often do you make a mistake and consciously decide, this one’s not worth criticizing?

And of course, how often do you make a mistake and consciously decide, this one’s not worth criticizing?

Here are some of the most common negative automatic thoughts2 — which ones have you experienced?

All-or-nothing thinking: You see things in black and white categories. If your performance falls short of perfect, you see yourself as a failure.

Overgeneralization: You see a negative event as a never-ending pattern of defeat.

Mental filter: You pick out a single negative detail and dwell on it exclusively so that your vision of all reality becomes darkened, like the drop of ink that discolors the entire beaker of water.

Disqualifying the positive: You reject positive experiences by insisting they “don’t count” or “it wasn’t just me”. In this way, you maintain a negative belief despite it being contradicted by your everyday experiences.

Jumping to conclusions:

(a) Mind Reading. Concluding that someone is reacting
negatively to you, and you don’t bother to check this out.

(b) The FortuneTeller Error. Anticipating that things
will turn out badly and feeling convinced that it’s doomed..

Magnification (catastrophizing) or minimization: You exaggerate the importance of things (such as your goof-up or someone else’s achievement). Or you inappropriately shrink things until they appear tiny (your own desirable qualities or the other fellow’s imperfections). This is also called the “binocular trick.”

Emotional reasoning: You assume that your negative emotions necessarily reflect the way things really are: “I feel it, therefore it must be true.”

Should statements: You try to motivate yourself with shoulds and shouldn’t’s, as if you had to be whipped and punished before you could be expected to do anything. “Musts” and “oughts” are also offenders. The emotional consequence is guilt. When you direct should statements toward others, you feel anger, frustration, and resentment.

Labeling and mislabeling: This is an extreme form of over-generalization. Instead of describing your error, you attach a negative label to yourself: “I’m a loser.”

When someone else’s behavior rubs you the wrong way, you attach a negative label to him: “He’s a jerk.” Mislabeling involves describing an event with language that is highly colored and emotionally loaded.

Personalization: You see yourself as the cause of a negative outcome.

So how do we change for the better?

Well, the BIG first step is recognizing it when it’s happening. If you’re on autopilot with your criticism and self-doubt, you need to become aware when it’s happening. Our goal is to become an impartial observer – not denying the feelings, not criticizing ourselves for feeling bad, just observe. Just be aware.

Pick a day — today works well, or tomorrow. Try to be aware of your self-talk — remind yourself throughout the day to be aware. Perhaps that means a sticky note on your computer or your notebook. If you’re finding it hard to catch yourself in the moment, spend a few days instead where you reflect back. In other words set two times each day for a 3-minute check-in.

Maybe you want to do your check-in at lunch and again on your drive home. During those 3 minutes, mentally review the day so far. What happened when you were unhappy, disappointed, critical? What were the negative thoughts? How were you feeling at the time? Make a note of these things (if you’re driving home when you do this you might want to dictate your thoughts on the handsfree recording app on your phone!).

The more you’re able to recall these times and to describe the feeling(s), the more you’re going to notice them the next time.

Start with articulating and acknowledging thoughts weighing you down–ones that don’t serve any useful purpose beyond keeping you stuck and then letting go with statements like, “I forgive myself for procrastinating” or “It’s okay for me to be angry.” These shortcut self-bashing and free up emotional resources.

The next big step is to challenge this thinking

One of the techniques we constantly use when helping people lead others is to ask those other folks open-ended curious questions. So, we recommend the same things for ourselves. When you think “that was a lousy talk” or “you should have seen that coming” or any of the others up above, ask “Oh, is that so? What makes you say that?” And then continue questioning yourself — be rigorous in your debate — challenge that negative voice to honestly justify itself.

Here are some examples:

  • What if things are better than I think? What am I depriving myself of?
  • When have I felt this way before, and realized later than everything was better than I thought?
  • So what if [insert worse case scenario] happens?
  • How can I…?

Focus on progress, not perfection

Another technique is to imagine someone in your life whom you care deeply for — your life partner/spouse, your adult child, your best friend, your closest confidante. If they told you they were feeling this way about themselves and they were criticizing themselves this way, what would you tell them? What would you say to help them see their positive progress, to help themselves see how good and capable they are?

Now tell yourself that. Be sincere.

Coach’s Questions

Where are you being tough on yourself? What steps above are you willing to try to make things better? What’s waiting for you if you let go of this?

(1) Harvard Business Review, March 22, 2017 “Difficult Conversations: When Your Toughest Conversations Are the Ones You Have with Yourself”
(2) Burns, D. D. (1980). Feeling good: the new mood therapy. New York: Morrow.

How great leaders get beyond their to-do list

Remember that time when smartphones weren’t a thing? When we would go home at the end of the day and check our messages on the answering machine?

When our time out in the world was spent in that place, in that moment instead of being pinged by 117 notifications at any given time?

No question – our time is strapped! Without exaggerating, our attention is being pulled in multiple directions at almost any given time.

We have a list of things to do at home, a list of things to do in the car, a list of things to do at work – today, this week, this month, this year.

As leaders, though, isn’t our job to rise above the chaos of seemingly urgent and direct ourselves and our team to focus on the bigger goals, the long game, the right direction?

As a leader, I’m willing to bet you’re strategic, you’re a thinker, you’ve got vision.

But, the reality is that all that vision has to be implemented and in many cases, you have to manage the implementation too.

How, then? How do we lead the big picture while rocking the day-to-day details?

Here are four tips for getting beyond your to-do list.

1. Keep ONE to-do list

I know this sounds big but stay with me.

When we have multiple to-do lists across multiple applications, notebooks, and physical locations, it’s very difficult to know if the thing you’re working on is the best most important thing to focus on.

And, focusing on the right thing at the right time is what great leadership is made of – it’s how you move beyond reacting to tasks in your day.

So often I see clients with lists in their email, a random document, an app on their phone, the platform of choice at work, calendar appointments, etc.

Centralizing to-do’s allows you to prioritize tasks amongst each other instead of prioritizing in silos.

There are a lot of ways to accomplish this and it varies based on the type of work and life tasks that you need to manage — and if you’re a paper and pen person, stick with it but carry that one list with you.

Or, if you’re willing to jump into using all that tech to your advantage, there are a few (free) tools that you can use to get all your to-do’s in one place and prioritize accordingly.


Todoist is a simple to-do and task list manager with a beautiful user-interface that allows you to add tasks, assign deadlines, set reminders, use labels and filters, and syncs across devices.

I use Todoist and find it the perfect place to store and manage all my to-do’s.

It syncs instantly between my desktop, my laptop, my iPad and my iPhone, along with my google calendar. Sounds a bit much, but it guarantees I have one organized list, everywhere I go.

Sounds a bit much, but it guarantees I have one organized list, everywhere I go.


Similar to Todoist, Wunderlist allows you to set up projects, assign due dates, collaborate and reorganize all of your to-do’s in one spot.

Also, syncs across devices and integrates with dozens of other applications so you can automate your task management process as much as possible.


Asana falls more into the project management category but is super effective for task list management.

You set up various projects with tasks within and then manage your tasks from a central “my tasks” view where you can drag, drop, and reorganize based on the categories of “Today,” “Upcoming,” and “Later.”

Do you already use a few different applications and you’re interested in being able to see everything in one place automatically?

Check out Taco. It pulls everything from 40+ services into one list for you to reorganize as you like.

Now, your ONE to-do list doesn’t have to be a digital but I recommend that it is so that you can easily carry tasks forward, rearrange, and reprioritize as needed.

I would also encourage to choose something that has a friendly smartphone application so you can add to your ONE to-do list on the fly and not have to worry about reconciling it later.

2. Determine your next day’s top three tasks at the end of every workday.

Momentum is incredibly important for staying focused and continuing to build on accomplishments and progress day to day.

A quick and effective way to make sure that you can hit the ground running (in the right direction!) each morning is to set the next day’s top three objectives at the end of each workday.

When I was working in the Privy Council Office with the federal government, we had to remove all confidential information from our desks each night, and lock it in our super-secure, heavy lead, combination-lock filing cabinets.

Given the work I was doing, that meant pretty much everything had to be locked up at night.

Now I didn’t know it at the time but I have a bit of ADD — I can get distracted by what’s in front of me and I easily forget about what’s not.

That’s not good when there are important and sometimes urgent state secrets, locked away in a cabinet. So, I got in the habit of making myself a list each night before going home.

In my case, the list had to be a bit cryptic so it could be left out, but basically, it summarized, in order of importance, everything that was still hanging over me and needed my attention in the morning.

This solved the ADD problem of “out of sight, out of mind” but it also delivered a few unexpected benefits:  

1) I felt a sense of comfort and ease going home each night — knowing the desk was clear, the office was tidied up, and everything I needed to remember was spelled out for me on a list –  I could literally let go of work, and have a life;

2) I arrived to a clean, organized office each morning which lifted my spirits and removed the “weighty sigh” that comes over me when I arrive to a desk piled with stuff, and;

3) It made me more strategic than ever before because the list of priorities, in order, was literally right in front of my nose as I started every single day.

Block out time each morning to complete most important – not the most urgent, but rather the bigger, important, actions, allows you to hit the ground running and it saves precious time figuring out where to start.

3. Do a weekly brain dump

We all know that feeling of millions of thoughts swirling around and the idea of organizing and prioritizing it all.

Especially as strategic and visionary types – there are so many worthwhile projects and ideas that we’d love to get to that just seem to be pushed back or forgotten in order to face the demands of the day.

It’s easy to do. Putting fires out SEEMS more important than that strategic project that might shift culture, or increase revenue or create more meaning.

But, it’s simply not. It’s crucial to make space for the big picture projects that will ultimately make more of an impact on organizational success.

One way to keep your eye on the big picture is to do a weekly brain dump (maybe at the end of the day on Friday).

You can keep it as a project in whichever to-do list tool you use and take the time to list out all of the things that you’d love to get to but just haven’t been able to take action on yet.

Once it’s recorded, you can assign a date to look at it again or, better yet, decide the next action step that you need to take towards said goal and schedule it.

Not only will this help you move from reactive to proactive, increasing your focus on the big picture and getting you off the to-do treadmill, it’ll lower stress and free up headspace knowing that you’ve captured those items in your system.

4. Create a weekly creativity/vision time block

To take the brain-dump activity even further, schedule a non-negotiable weekly visioning session to create space for guilt-free attention on big-picture work — this is a good time to do your thinking about the brain-dump but also to reflect on how the tasks are getting you to your bigger goals (or not).

A number of our clients have found they like to stop somewhere for a coffee on the way into the office on Monday.

Many tell me if they get to the office, it’s too late — their schedule is jammed, urgencies arise, etc.

But, booking their day to start a bit later than usual, and then using that time to savor a skinny, non-fat, high octane, mocha frappa something — while reflecting on the big picture, day-dreaming a bit, making some notes, helps them boost their success all week long.

Coach’s Questions

Where are you focusing on the urgent and missing the important?  What prioritizing techniques resonate for you?  And, when are you going to start using them?