What Every Boss Wishes You Would Do When You Royally Mess Up

I was waiting in a client’s office.  She was running late from a meeting with her boss.

After walking in, closing the door behind her, and giving me one of those appropriate corporate hugs she said, “I am in big, big trouble.  I mean it is bad, Ryan.  I have really failed.”

Then she described how she screwed up.

It was bad.

Now mind you, she is at that level in a Fortune 500 company where you never have to guess about competency.  If you get to that level, you have gone through a tremendous vetting process.  So for her, there was a lot more fear involved as she struggled with how to rebuild credibility.

Moreover, her boss has a reputation for being completely insensitive, harsh, and lacking in grace.

She debated as to whether or not she could fix it before anyone knew.

But when she thought through the question of what she would want her direct reports to do if they were in her shoes, she decided she would want them to tell her.

Then she flipped back.

She wondered if her boss’s reputation did not warrant that she hide the error.

Later she realized that if he ever found out, she would probably be terminated because he would feel he could not trust her again.

How many of us have been in similar shoes?

In toxic work environments, there is a high level of manipulation, covering up, blame-shifting, office politics, positioning, and often backstabbing.  Toxic work environments are toxic because managers have not embraced their responsibility to create a culture where it is safe to risk for the greater good or to own our mistakes when they are made.

If you find yourself in a toxic environment, the plan that I present below will feel really uncomfortable.

I hate to say it, but if your work environment is toxic and there is no desire on the part of your superiors to move towards health, I really hope you can quickly find a place where your gifts are valued and the environment is healthy.

Fortunately for my client, despite her boss’s reputation, the overall work environment is fairly healthy.

Here is the plan that my client and I came up with.  It worked for her, and I hope it works for you:

1. Fully own your mess-up, with no “marketing” whatsoever.

The conversation can open with the following: “Bob, I made a real mistake.  I did X, and it cost Y. I apologize.”

Do not try to blame-shift, minimize, rationalize, or “market” what happened.  Be direct.  Be succinct.  Fully own it.  And don’t forget to apologize.

Make sure to let your boss know that you will also be owning it to whoever else is involved.

If you do not own it, know that if it is major, it will probably be discovered and your boss will be more likely to fire you because your deception has led to a breach of trust.  Toyota Chairman Katsuaki Watanabe explains it best in an interview with Harvard Business Review:

“Hidden problems are the ones that become serious threats eventually. If problems are revealed for everybody to see, I will feel reassured. Because once problems have been visualized, even if our people didn't notice them earlier, they will rack their brains to find solutions to them.”

2. Give alternatives for how you think it can be resolved.

“I have a few suggestions for how to resolve it….” This part of the sentence shows them that you are coming up with options, not just the problem.  It shows that you have fully owned it and that you own the ripple effect.

3. Ask them for input and collaborate to build a solid plan.

“...And I am looking for your insights to build a plan that will bring us to resolution.”  This second part of the sentence encourages your boss to partner with you to solve it.

Your boss may have an initial reaction that seems negative.  However, the higher up you go in a large company, the higher the emotional intelligence tends to be.  So don’t be surprised if they regulate their emotions and even move towards protecting you, and showing you grace.

4. As you and your boss work to develop the plan, pay close attention to why your boss is suggesting what they are suggesting.

Hopefully, you will begin to brainstorm together as to how to handle the situation.  Your boss will want to hear your options first, which will help him/her to see your heart better.

Then your boss will probably refine the option they think is best.

Seek to understand the reasons for the suggestions they are giving you.  The “why” will give you insights that you will be able to use throughout your career.

You will learn how they view an issue, how to protect corporate culture, and, hopefully, how to extend grace when those under you fail.

Be sure to share how you plan to prevent yourself from making such a mistake again.  Never just say, “It won’t happen again.”

Ask for their input. You can say, “In the future I will pay attention to the triggers that led me to lose my cool” (preventative), but then ask if they see things you could do that would encourage growth, like signing up for a course on how to build better work-relationships, for example.

5. Afterward, continue to prove that you’ve grown from your mess-up.

Fully commit to implementing the plan you discussed.

Execute with all you have.

Use the insights that you learned in the brainstorming session in multiple contexts.

People who have grown from mistakes don’t live in self-condemnation.  Instead, they forgive themselves and enjoy the restoration they have been given.  Be grateful for it.  Share your gratitude with your boss and even others on the team, if it is appropriate to do so.

You are still competent and valuable.  You just screwed up and proved you are human.  Don’t be surprised if your boss and others pull closer to you as they see you display the humility and gratitude that come from growing through a mess-up.

You will rebuild credibility faster by having multiple small wins than one big win.  So don’t look for the home run; focus instead on consistent base hits.

As an FYI, the next time I met with my client, she said her boss had done the unexpected.  He really jumped in to protect her.  He was completely gracious and even shared one of his own big failures.

Chew On This:

• What are you hiding that needs to be owned?  What would be the consequence if it were discovered?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

Ten Actionable Steps To Facilitating Great Skip-Level Meetings Part 2

In Part 1 of Ten Actionable Steps to Facilitating Great Skip-Level Meetings, we discussed how despite many attempts Bob, a business owner, could not get three of his eight teams to have higher engagement.  He knew he was missing the front-line’s perceptions of what was dragging down their engagement.   

In Part 1, we discussed the first four Actionable Steps.  They were:

• As the leader, sit down with your manager and get the manager’s buy-in for a Skip-Level Meeting.

• If you haven’t communicated much two levels down, start doing so months before the Skip-Level Meeting is solicited.

• You and manager send a joint email to the manager’s team.

• Create a safe environment.

Below are six other actionable steps Bob took to facilitate great Skip-Level Meetings:

• Ask open-ended questions and do not judge or correct the answers. Just empathize and take in the responses.

This is a time when you want to turn on your curiosity and eliminate all judgment.  

As best as possible, ask questions from a positive vantage point. Some examples include:

• What do you like most about being on the team?
• What tools or resources have you found most helpful?  Why?
• If you could wave a magic wand, what is one thing you would do to make the team even better?
• Tell me about a time when your manager was most helpful to you.
• If you were in your manager’s shoes:
  • What would you be focusing on?
  • What would you be doing more of?
  • What would you be doing less of?
• What questions haven’t I asked that I should have asked?
• What can I answer for you?

• Utilize strategic storytelling.

When you sense one of the responses has a story behind it, ask for the story behind it.   Tell them what themes you hear in their story.

Find an opening to share a story that cements a key message or belief you want them to walk away with.  Ask them what they got from your story.  

• Ask clarifying questions as you go.

If you are unclear about something they are sharing, ask questions until you are clear.  Among other things, asking clarifying questions shows that you value what they have to say and want to take it all in.

• Thank them for their time verbally and in writing.

Thank them for spending the time with you and share what you especially found helpful.  Assure them that you heard them and will take what they had to say seriously.  Let them know that you will be weighing what everyone shares with you, and that you will be discussing their concerns, in order of importance, as you coach their manager. Ask them to be patient as you implement.

Then the next day or so, send them a thank-you email. Let them know that if they have anything else to share, they should feel free to email or call you.

• Develop a strategy with the manager and execute.

Once you have interviewed everyone, look for themes and create a safe environment with the manager.  Share that you are looking to make things even better, and that you want their help in creating strategies to do so.

Discuss the themes you discovered with the manager.  

Gain the manager’s feedback on those themes.

Develop strategies to strengthen what could be strengthened and to meet the opportunities that were presented.

• Follow-up.

Decide with the manager how you want to follow up with the group.  You could send the group a summary of the key themes. You could also share what you and the manager will start to work on, and solicit the group’s encouragement and possible help.

Skip-Level Meetings can be an empowering, motivating, and informative way to increase engagement and move the business to new heights.

Chew On This:

• What would seeing your business from the eyes of your front-line do for you?

*This blog is a compilation of three different clients.  No one particular client is being singled out.

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

MBTI Bite: Three Tips for Working with P's

Many of the P’s (Perceivers in Myers-Briggs) I know have a duality about them.  On the one hand, they feel like they are a mess: they can’t seem to “get organized” or finish what they start.  On the other hand, when they are in their element and have room to just be, they can chill or be the life of the party.  They love that part of themselves, and those of us who are J’s (Judgers) love watching it. (Okay, to be completely real, we are envious of it.)

The P’s whom I have coached in corporate America mistakenly believe they need to hide their "P qualities” for fear that those qualities will hold them back from climbing as high as they desire.  However, nothing could be further from the truth.  They actually need to leverage those qualities, and we who are J’s can help them.

If you are working with a P, there are three tips for drawing out the best in them.

1. Set plenty of mini-deadlines ahead of the true deadline – P’s tend to work in bursts.  A burst magically appears about an hour before the deadline is due.  The amount of creativity which P’s show and the work they get done in that last hour is amazing.  J’s who are working with P’s or managing them often feel like the P’s are driving them nuts.  They wish P’s were more methodical.  If you are collaborating with a P, break down the project into multiple parts, then set clear and hard deadlines for each of the parts.  Make sure that you give yourself enough time at the end to refine the work that is being completed because P’s often wish they had “a little more time” to correct some of the pieces.  By leaving time to refine, you can both work on sharpening it.  You will appreciate the ingenuity a P brings to each part of the project.
2. Don’t suffocate them with a rigid schedule – J’s like to be scheduled.  P’s like to be open-ended.  Many companies I work with have so many meetings that a P tends to feel suffocated.  The calendar is full, which works against their natural desire to be flexible.  If you want a P in a meeting, please make sure the meeting is essential.  All of us need space to think, plan, and review.  P’s also need open-ended space, where they can draw out their gifts for the good of all.  Granted, the higher they climb, the harder it will be to find open-ended space.  However, I would encourage P’s to carve out at least a two-hour, non-negotiated block in their week for free thinking.  Ideally it should be more, but even with that much, they will accomplish so much more than without it.
3. Feed P’s with knowledge, wisdom and tips and watch them brilliantly mix and match them at the right moments – P’s know how to wing it.  The sharp ones are able to pull from multiple sources in order to wing it well.  They can adjust on the fly and come up with brilliant ideas that seem so well-thought-out, you would think they had been thinking on it for hours.  What P’s often need in order to nail this gift is more knowledge, wisdom, and tips.  If they are N’s (iNtuitives), they could accomplish this through reading the first and last paragraphs of an article and scanning the rest.  If they are S’s (Sensors), they typically they want details.  I would suggest they become thought leaders in the most essential part of their role.  If they set aside even 30 minutes per day to accumulate more knowledge, wisdom and tips, you will see it pay off dividends in meetings where their wing-it skills are praised.

All personality types are equal.  None are better than the others. We need to leverage each other’s natural gifts in order to accomplish the greater good.

Chew on This: How do you need to adjust for the P’s who are on your team?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

MBTI Bite: 3 Tips for Working With "Sensors" ("S" in Myers-Briggs)

When I was first getting into executive coaching, I could not tell the difference between Myers-Briggs preference types.  I began working with a client who was a high “S” (“Sensor" in Myers-Briggs language).  Sensors are typically concrete.  They love details and facts.  They often search for all available data before making decisions.  They also tend to be literal in their language.

I am a high “N” (“iNtuitive").  Us N’s tend to love the big picture.  We are fascinated by ideas and new possibilities.  We typically tune out when a “ton of details” are being discussed.  We are known for seeing patterns and principles behind the data and jumping to conclusions.  While we may be much more accurate than not, at times we do jump to the wrong conclusion.

Based on the descriptions above, how do you think our first meeting went?  

You guessed it.  He was going on and on with details and facts.  I wanted to “cut to the chase.”  I interrupted at times.  I tried to steer to conclusions sooner than he wanted.

He did not feel like I heard him.  I did not feel like we made much progress in that meeting since we did not complete his stated goal for that first meeting.  I am fairly sure he had doubts as to how well we would work together.  I was confused as to how communicate with him.

A mentor who was well-versed in Myers-Briggs helped me understand my client a lot better.

There were three tips my mentor and I came up with during our meeting that I want to share with you in case it helps you with what you do.

What To Do When You See the Signs That You Are Working with a Sensor 

1. Send out an agenda ahead of your meetings with them. When creating an agenda for an “S,” especially a high S, make sure that it leaves plenty of room for the exploration of facts and details.  If the person you are meeting likes to plan and be prepared, they will often start to gather the facts ahead of time and will start to sift through them on their own.  If you tend to tune out when there are too many details, turn on your curiosity.  Say to yourself, “I want to understand how he comes to conclusions.”  There may be times when you need to set a limit to the amount of exploration, but allow yourself to understand them.


2. Start with the highest priority item. Even if you set an agenda that has plenty of room for the exploration of details, you may find you don’t get through all the items on the agenda.  Often times the first item on the agenda gets the most amount of time.  Then each successive item gets less and less time as the meeting winds down.  Some items could get postponed.  Therefore, always start with the most important item.


3. Make things tangible.  Get practical with Sensors as soon as you can.  Sensors take things in through their five senses.  Leverage that.  Show them charts and drawings.  If there are videos or audio recordings that can be used in a meeting, use them.  Be specific.  Say what you mean.  Mean what you say.

If you practice adjusting your style to another it will go a long way toward building a great relationship.

Chew On This: Which stakeholders are High S’s?  Choose one.  How will you adjust your communication style when you engage them?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

When Two Departments Collide

What is it like for you when you know two of your departments are clashing?  What’s it like watching the waste, turnover, and disengagement?  What have you tried to do to bring unity to the company?  Have you grown frustrated?  Have you become resigned that it will just be that way?

You are not alone.

Workplace conflict across departments is common and, unfortunately, extremely costly.  Often times the way leaders try to resolve these inter-departmental issues is by focusing on the present situation instead of focusing on the interpersonal dynamics.

For example, let’s say a marketing department comes up with a slick campaign that requires a little more budget, but the finance department won’t release the funds. Maybe a leader would come in and just try to resolve the issue by seeing what the options are for finding the funds from less important projects or by trying to reduce the campaign.  Whatever solution is found, one department is likely to be disappointed.

Instead of focusing on the present situation, focus on the heart.  Get each department to clearly articulate what their core drivers are.

Discover Core Drivers

One way to discover the core drivers is by asking marketing what the slick campaign represents to them.  Ask finance what the holding of the funds represents to them.

At first they may think that what you are asking for is obvious to all, but ask them to really get to the core.  Listen for values that can’t be further reduced.

So, for example, the core is not about making more money or staying on budget.  The core is about something deeper.

An acronym that I use to help me know when a team has gotten to the bottom of it is the acronym “SLAVES.”  It stands for:

• Security
• Love
• Acceptance
• Value
• Enjoyment
• Significance

Listen for a tailored message that encompasses one of these six core drivers.  Make sure both departments understand each other’s core drivers.

Have each of them spell out what it means to them when the core driver is achieved.

Now, once you know what the core driver is, address the problem from that perspective.

Conflict Resolution

If achieving high levels of enjoyment is what drives marketing, then have marketing AND finance partner together to see how else this high enjoyment can be achieved.

If finance wants security, have both finance AND marketing work on solutions for they can achieve greater security for finance.

Both working together to generate solutions on behalf of the other will lead them to learn how to use their differing skills, personalities, and drives for each other’s benefit.  This will bring unity.

At the end of the day, destructive workplace conflict is a people issue more than a philosophical issue.  When people are united and know they have each other’s best interest at heart, constructive conflict can help to generate the best possible solutions for all.  High performing teams know what that is like.

To resolve destructive conflict quickly, define what the core drivers are.  Then have those in conflict partner together to find ways to meet those core drivers for one another.

Chew On This:

• What is your core driver?


If you have any questions feel free to email me at  ryan@ryancbailey.com or call (404) 421-8120.

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.