The 2 (+1) Most Important Work Relationships to Build (and it isn’t with your boss)

You may believe that your boss holds the key to your career growth, but he or she isn’t the only one you should be investing your time with. Here are the key types of relationships you’ll want to cultivate at work:

Mentor: a mentor is someone who has been in your shoes and is available and willing to provide you advice as you grow in positions of increasing responsibility. This is someone who wants to give back and sees you as a high potential talent. They may be someone higher up in your department or division, or someone at a senior level in a completely different discipline than your own. Ideally, your mentor will meet with you at least once a month for an hour to check in, learn about your most recent wins and challenges, and provide advice on how to navigate current events. The alternative perspective they can provide is deeply valuable.

Bonus points if you form a relationship with a mentor internal to your company and one external. The external mentor can also serve as a valuable networking agent when it comes time for you to make a career move.

To kick off a relationship with a mentor, send an email to the individual you’d love to learn more from and inquire if they might have the capacity to serve as your mentor. Chances are they’ll be deeply flattered.

Stakeholder: a stakeholder is someone who is more senior to you within the company who is also your advocate. Behind closed doors, in key organizational meetings, a stakeholder is someone who will actively advocate for you to be promoted into positions of increased responsibility. They are someone who is familiar with your personal brand and want to see you take on more responsibility because they know you’re more than capable. An ideal stakeholder is a leader in a department you work closely with who is familiar with and admires your contributions and work ethic.

To develop a relationship with a stakeholder, think about key senior people within the company you admire. Cultivate relationships with this leader by being the best version of yourself possible. Show up each day and be productive at work, in meetings, and in your contributions.

How is this different from a mentor? A relationship with a stakeholder is more organic and natural. You won’t begin an email to them with, “I’d like you to be my stakeholder,” as you might indicate in a note to a prospective mentor. A stakeholder relationship happens more fluidly. It happens through an email you might send to them about an insightful article you thought they’d find interesting, thanking them for the input they provided in a meeting, or complimenting them on their team’s contributions and the great impact it had on you. This relationship happens over time and as a result of many positive data points about you and your contributions.

Separate from these two key relationships, and one not to be overlooked, is a relationship with your company’s CEO. The CEO is a brilliant person to be able to observe and form a relationship with. Make sure your CEO knows more than just your first name.

In many companies, access to the CEO isn’t possible. Perhaps she works in another city or the company is really just too large for you to feasibly get in front him/her. If it’s not the CEO, then why not your boss’ boss’ boss’ boss? Your mission is to identify the most senior individual within the company you have access to who you can also build a mutually beneficial relationship with. This person could be your mentor, but if nothing more, this individual will be a valuable person for you to observe during meetings, make note of how they deal with challenging issues, how they carry themselves each day and how they build relationships.

In the title you’ll note that I suggest your most important relationship isn’t with your boss. Why is that? Certainly, it’s an important relationship and one you should focus on ensuring is the most positive and productive it can be. That said, for true and significant career progression, it’s important for you to cultivate relationships at a level outside of your boss so you can promote your personal brand external to your current position and department, and develop advocacy.

So, where do you start? Your focus for the rest of the week is to get out from behind your desk and start engaging with interesting, available, and outstanding leaders you can learn from. Bring some unique ideas forward … and don’t be afraid to put yourself out there. You’re a rising star, and it’s time to get the visibility you deserve.

– Jackie Simon

3 Things You Can Do Right Now to Get Ahead

Thank you note

  1. Always write thank you notes. Handwritten is best. Leadership is about demonstrating gratitude, kindness, and thoughtfulness to those around you. Whether one of your team members has gone over and above on a project or you received a raise or a special introduction to a key contact, show your appreciation for the extra steps someone else took for you by graciously thanking them.
  1. Get that difficult [email, phone call, conversation, meeting, decision, discussion] out of the way first thing in the morning. Why let it hang over your head all day (or week or month)?
  1. Act now; apologize later. There will be times that you’re called to make a big decision or take action without having key information available or the opportunity to work through known channels or procedures. Do the best you can with what you know and take action. Even if things don’t go exactly as planned, you’ll very likely navigate the unexpected successfully and learn a lot along the way.

That’s it, you ask? That’s it.

Next week, we’ll talk about the most important skill set you should develop for significant career (and compensation) advancement.

– Jackie Simon

Why the Difficult Employee Isn’t Being Fired


To start, this post isn’t about the common characteristics difficult employees share. This also isn’t a post about how to know whether or not you should fire an employee. What this post is about is why leaders don’t fire difficult employees even though they know they should. Donald Trump makes it look easy and swift. That’s not always the case.

Here are the most common themes I’ve found around why leaders don’t fire their problem employees. The employee:

  • has been with the company for years;
  • is the only one in the company who knows how to do specific tasks. Firing the employee means there is a body of work no one else in the company knows exists or how to complete;
  • is deeply entrenched in systems, processes, or finances. The leader perceives letting the employee go is far too much of a risk or liability to the company;
  • has close relationships with key clients or team members. The leader is too focused on the potential disruption to the team or business;
  • is unapproachable, dramatic, or negative. Therefore, the idea of a termination meeting is quite unsettling to the leader (if the employee gets upset about constructive improvement feedback, how might they react when they learn they’re being fired?)
  • is likened to a unicorn. The leader honestly believes it will be next to impossible to hire someone else to replace the employee.

But, these reasons don’t come close to the number one reason leaders don’t fire their difficult employees. The number one reason actually has to do with the leader than the employee. The reason? The leader has never fired someone before. The leader’s lack of firing experience is the reason an employee stays and the team, business, and company are negatively affected in the meantime.

Essentially, the unknown for the leader, meaning the “how” to fire an employee is too scary to confront. As a result, the difficult employee stays with the company for weeks, months, and even years.

Removing a difficult team member from an organization is just one key area of responsibility for a leader to overcome in order to take the team and business to the next level. Until that’s done, the leader essentially agrees to hold themselves and the team back. At that point, it has nothing to do with the challenges the difficult employee brings to the business and everything to do with the leader’s reluctance to fire the employee.

As leaders, it’s our responsibility to do the hard but right thing every single day.

Next week, we’ll talk about how to identify if you’re getting in your own way and the potential price you’re paying as a result.

– Jackie Simon

Top 10 Leader Faux Pas


We all need to brush up on our leadership etiquette. Here’s a quick list of key areas we all fall victim to from time to time.

Think of your actions over the past week as you read the list below and score yourself 5 points for each “Yes” and 0 points for each “No.”

  1. Arriving late.
  2. Checking your phone/laptop during meetings.
  3. Lacking an agenda.
  4. Failing to make direct eye contact.
  5. Neglecting to greet co-workers when you arrive at work.
  6. Taking calls on speakerphone when others are within hearing range.
  7. Walking ahead of team members instead of side-by-side.
  8. Embarrassing people publicly.
  9. Interrupting others.
  10. Forgetting to say “please,” “thank you,” and “excuse me.”

Your Score:

How’d you do?

If you scored fewer than 10 points, I’d say you’re conscientious of your actions as a leader. Great job! Keep your self-awareness high by revisiting this list from time to time.

Did you score more than 10 points? Now is a great time to regroup, think about how you would like to be perceived as a leader, and start making some key changes so you’re bringing your best self to your team. Remember, being respected as a leader means treating your co-workers with the same respect.

Did you recently correct a leadership faux pas? If so, tell me about it!

Next week, we’ll address a topic on everyone’s mind: how to ask your boss for a raise.

– Jackie Simon

Scooch Your Butt off the Edge

Whether it’s a career change, starting a business, buying a house, moving to a new city, going back to school, or any number of life changes, you’ve had it in your mind for a while to do something BIG. You know what you want and how to get there but you haven’t made the leap. To gain in bigger and more fulfilling ways, you must risk. There is no other way around it. Recognizing that you have a tendency to shy away from risk is the first step to changing. To overcome your fear of risk, you must understand what is driving your fears and then brainstorm ways to overcome them. Make a change, try something new, keep trying, and enlist your friends and family for support along the way. Now is the time! Scooch your butt off the edge. No matter the end result, you will be all the better for it.

(You have spinach in your teeth.)

You’d rather have me tell you, wouldn’t you? I often get asked by leaders about the best way (and time) to give feedback to team members. “Hey Jackie, what do you think of the feedback sandwich?” “Hey Jackie, what do you think of feedback? Shouldn’t it be in the moment?” or “Heyyyyy, Jackie. How about feed forward, you know, like pay it forward? What do you think?”

When’s the best time to give thoughtful, considerate feedback aimed at helping a colleague, direct report, or even a friend improve? The answer is simple. When they’re ready for it. Obviously you wouldn’t tell a friend she has spinach in her teeth when she’s got a mouthful of food. She’s still busy processing!

Feedback is best received when the recipient shows signs of digestion — being ready and open.

Q. What does “ready” look like?

A. The individual is truly in a place where she/he looks confident, secure, and at ease.

Q. What’s the best kind of feedback to give?

A. Remember that the whole point of feedback is to provide information that will help someone do more, do better, and be happier.

Q. Do I have to give feedback?

A. We all need feedback. I’d much rather know if I have spinach in my teeth than stand in front of the world, smiling with a big wide grin. But wait until I’m done chewing. And make sure it’s focused on the spinach, not on my smile.

Because I want to be able to take my big, wide, beautiful grin in front of the world again, without the spinach this time, and smile even bigger and brighter.

– Jackie Simon

“I’ve always known _____ about myself”

A friend of mine remodeled her parents’ spare bathroom. Tore down the dated wallpaper. Repainted. Removed knick-knacks. Added fresh flowers. Changed the towels and rug. Then, inspired by the “before and after” of her work, she moved on to the kitchen — painting the 1970s dark brick backsplash a softer cream color.

She was 16. Her parents were out of town.

Gutsy move. But clearly she was compelled by an unstoppable force. Even at a tender age, she knew she loved “making things better,” decorating, designing, makeovers, and remodeling. Today she is in the creative world, making things better, designing, branding – and gets paid for it.

How often have you found yourself saying “I’ve always known ____ about myself”? How young were you when you realized your true calling? When it comes to relationships, career, hobbies, or interests, tune in to what you’ve always known. At the core is a major clue to something you were born to do.

– Jackie Simon

5, 3, 90

I’m a big fan of numbers. Not in a math kind of way, though. Geometry, what?

I love the relationship of numbers, patterns, and how numbers can create meaning for people. As a kid, I liked to break down groups of numbers to make them both familiar and memorable.

Now that I have been coaching for awhile, I’ve found that numbers are an important part of the work I do with clients to create change. Goal setting, as an example, requires just the right number by person. Setting too many goals can be incredibly overwhelming for some. Setting too few goals may not strike the right chord of accomplishment for others.

Here are 3 numbers I have grown to love as a coach:

5, 3, 90

I use these 3 numbers with people to set the following:

  • 5 goals for one year
  • 3 actions
  • 90 days

So, how does this work exactly? When working with a client, we discuss what matters most to him/her and the areas they wish to change or improve. We then set 5 goals for the year in the direction of that change. Then, we reflect together on the goals to determine 3 actions that, if taken over a period of 90 days, puts them on track to achieve those 5 goals over the course of the year.

For 90 days, the individual focuses on completing those 3 actions. Then, as the 90 days wrap up, we reflect on the next 3 actions that need to be taken over the upcoming 90 days to keep them on track to achieving their 5 goals for the year. Rinse. Repeat. Four times.

The purpose of this approach is help people to maintain discipline and momentum over a shorter timeframe. Ninety days is a reasonable amount of time to stay disciplined and focused in any particular area while not losing sight of what matters most.  Instead of trying to tackle 5 goals for a sustained amount of time (365 days), 90 days keeps it all front and center. If you’ve tried P90X, you may see my point.

As we gear up to the first of the year, what are 5 goals you wish to accomplish? What 3 actions will you take between January 1 – March 31, 2011 to keep you on track to accomplishing your goals?

Putting it on the Backburner

When experiences are new or challenging, we have a tendency to put things on the backburner until we really must address them to move forward.  The same is true of my personal experiences in business.

I’d be lying if I tried to convince you that the past two years have been easy. I didn’t just decide to start the business and then focus every single resource, skill, and minute I had on it. There have been plenty of “stops and starts”, “can’t do its”, “things are good enough the way they are so why go changings?”, and “I just don’t want tos”. My list of excuses was endless and my fear of failure has been significant. I actually could have fast forwarded through the launch of the business in well under a year but there were periods of fear and uncertainty that held me back.

As time passed though, it became more clear that doing nothing for the sake of not changing just wasn’t good enough. I realized that keeping life “as is” meant that I was effectively putting my life on hold. As time passed, I realized the significant impact that I was having on my career and other areas of my life by sitting still. I also found that I wasn’t able to shut down my own ambition. For as strong as fear of the unknown and uncertainty can be, ambition and motivation can be even stronger. I simply wasn’t able to keep shutting the door on something that I believed so strongly in and wanted to do so much. Eventually, ambition overcame the fear of failure enough so that I made the break and decided to go for it.

To overcome the fear, I made a commitment to myself to do something in pursuit of the business every single day. Whether it involved reading, writing, networking, coaching, or business planning, I signed up to do one thing every day. It didn’t matter if I spent 5 minutes or 5 hours on any particular day, I committed to making something happen, no matter what, every single day.

What I’ve learned along the way is that taking action, no matter how big or how small, helps me to overcome my fear, make progress, and feed my ambition. Each daily action helps me to grow, change, and move in the direction of where I want and choose to go. It keeps the “can’t do its” at bay and helps me put a tight lid on the “you’re never gonna make it happens”. Each day belongs to me and I get to define and dedicate my effort to moving in the direction I choose every single time.

How about you? What do you do to move forward despite fear or uncertainty?

Doing What I Love to Do

A funny thing happened along the way to figuring out what I didn’t want to do in my career. I figured out what I wanted to do. And, what I loved to do.

For many years, I struggled with finding my path in life. I would go for days and months accomplishing great things and moving forward in my career, but never feeling my career was truly an extension of me. I knew what I did well and often found myself in positions that capitalized on my strengths. The disconnect was that I didn’t really enjoy the work, even though I was utilizing my strengths. I was caught in between the things that I could do very well yet never feeling complete joy and satisfaction in my work.

As my career progressed, I found myself feeling lost. I had achieved all the common milestones: finished undergrad, landed starter job, left starter job for the next job, started and finished graduate school, and got promoted. I kept working for the next promotion and then kept working for the promotion after that. Once I finished grad school and moved up within the company, I found myself stalling and feeling sidelined. Each opportunity leveraged my strengths yet brought me face-to-face with work that I didn’t completely love.

During one particularly stressful period at work, I became more discouraged and frustrated. I spent numerous days mulling over the work that I disliked and what I didn’t want to do in the next job. I knew that my career path at some point would involve owning my own business, but I struggled to figure out what that business would look like. And then, one evening, as I was standing in my kitchen gazing out the window, it hit me. It very honestly and really hit me. For all the days and months I had spent focused on what I didn’t want to do, and frankly, what I absolutely disliked doing, I made a simple shift in my thinking that allowed me to discover my path and my purpose.

The simple shift that I made involved framing the question differently than I had up until that evening. Instead of framing the question in the negative, I shifted my thinking to “What can I do?” and “What would I really love to do?” and “What gives me energy?” and “What is my purpose?” And that’s when it hit me. The light literally went on and there was a momentary flash. I remember feeling really happy and really scared all at the same time. In that moment, I was able to connect all the pieces of what I loved: working with people, serving as a resource, advising and coaching people to solve business, leadership, and career challenges, and helping people to grow personally and professionally. I’ve always been an avid gardener with a real love and passion for cultivating seeds into beautiful flowers. Coaching represents all the things that I love about gardening and gardening is everything that I love about coaching. So it all began.

I’d like to say that the very next day the business was launched. The reality is that it took two years from that evening. I needed time and space to build a plan, plant seeds, and grow into doing what I love. It was a pivotal evening nonetheless and one that put me on the path to doing what I love. Today, not only am I running down that path, but I’m cultivating the business and career of my dreams and my life is fuller, richer, and happier for it.