Are You Getting in Your Own Way?

As a leader, you have an endless list of things that need to get done. On the list is strategy, leading and coaching, hiring and growing your team, budgeting, and launching new products and services. Most likely, these are the very things that fall last on your list because of other day-to-day odds and ends like putting out fires, solving problems, getting projects back on track, and resolving client or partner issues. The balance between the day-to-day activities and focusing on the big hits that move the business and team forward can be difficult to juggle.

If you find yourself spending most of your time on the day-to-day emergencies, it can be a sign that it’s time to make a few changes. But, how do you know for sure you’re misallocating your time?

Here are a few signs:

  • You’re staying late at work while your team ends their day at a reasonable time.
  • A team member or two have come to you requesting additional responsibilities to fill their day.
  • You find yourself logging in late at night to review work your team has sent you to take a look at. You spend the next hour or so reworking the deliverable.
  • You’ve caught yourself thinking, “If I want something done right, I need to do it myself.”
  • You cancel one-on-one meetings with your team members, often at the last minute.
  • When ending a meeting with a direct report, your to-do list is noticeably longer than theirs.
  • The two-hour time block on your calendar to focus on strategic activities usually gets blown up by 9am to resolve the latest burning issue.
  • You’ve found the best time to get the big things done is Sunday morning while your family sleeps in.
  • You’ve postponed taking a day off numerous times.
  • You haven’t had a chance to review and map progress against your team goals for at least two weeks.
  • Your boss has hinted that you may not have the capacity to take on the next big initiative. The one you were most looking forward to.

On the surface, things are getting done. But not the big things. The projects and initiatives that will take you, individuals on your team, and the business to the next level are stagnant.

It appears to be the nature of the beast given your leadership role. What you may not see in the day to day, unless you look up from the weeds, is that you’re likely not leveraging your team effectively.

In short, you’re getting in your own way.

The difference maker here is learning to delegate. Realizing that it’s time to move over and teach others on your team how to take on greater responsibility. In turn, you’ll be able to do the same.

Your challenge for the week:

Pick five tasks from your list this week to delegate. Then, step aside as your team members take the lead. Will they have questions? Probably. Will they make mistakes? Maybe. Will you end the week feeling like you moved a big priority forward? Absolutely.

Let me know how it goes this week!

– Jackie Simon

One Bite at a Time

You’ve got a lot on your plate. Between work, home, family, hobbies, and other personal obligations, how can you possibly get [fill in the blank] done, too? Did you bite off more than you can chew? Where will the time come from?

Picture a waitress delivering a BIG platter of the most beautiful spaghetti you’ve ever seen. You’d never look at it and say, “Oh my! There’s no way I can do this. Take it away.”

Just as with time management, you’ve got to swirl a few noodles around your fork at a time. Then, when you’re maxed out, get a to-go box and save some for tomorrow.

What are the two most important bites you can take today? Get those out of the way. Save the rest for later.

(Hint: I’m free for lunch.)

– Jackie Simon

How to Lead Your Boss

We reflected last week on the importance of leading your boss to improve your own effectiveness. In a nutshell, by leading your boss, you’ll find that your job gets easier and you’re showcasing your adeptness to lead, manage, take on greater responsibility and get things done.

You may now be thinking more about leading your boss and how exactly to accomplish that. Here are some suggestions:

For the boss who micromanages:

Let’s say your boss gives you lots of projects but not the space to independently manage them. Once a project has been delegated to you, you find your boss remains in the picture, sending countless emails regularly to inquire about status, jumping in to respond to people on your behalf, and completing tasks before you have a chance to address them.

For this boss, you need to build trust and confidence with her. Show that you can more than competently take the reins. When you receive the next project from your boss, set up a brief meeting to review the project purpose, your approach, timing, and the tasks you’ll own. Clearly set expectations with your boss that her help isn’t needed at this time but you’ll be sure to let her know if and when it is. Then, take the lead. If your boss begins to interfere, pop your head into her office and confidently thank her for her help while assuring her that her help isn’t needed at this time. It may take a few instances of “correcting” your boss on running interference. If after a few corrections, your boss doesn’t seem to be getting the hint, set up another one-on-one to talk openly about the challenges you’re experiencing and to see if you can come to an agreement on mutual responsibilities moving forward.

For the boss who doesn’t effectively prioritize:

It probably feels like you’re spinning your wheels at work most days. One day the direction is blue, the next it’s red, and so on. This boss clearly has difficulty making up his mind. Or, he’s dealing with the exact same kind of boss you are. Someone at the top may be constantly changing objectives, making it a larger, cultural challenge.

To start, meet with your boss as close to weekly as possible to discuss current and upcoming objectives. The key to getting ahead on this one is that you’re taking the responsibility to set up and ensure consistent meetings with your boss to focus and prioritize. Discuss and agree to the priorities, and send a meeting recap. Then, if anything changes, meet with your boss again and lead a dialogue to understand what may be driving the change in priority. The key behavior in this situation is not to gather the changes and then head back out to implement them, but to engage your boss in a discussion about why the shift in priorities occurred. Without creating a perception that you’re a roadblock to change, you’ll want to engage in dialogue to demonstrate your deeper desire to understand what’s driving the change and truly chase the highest priority projects. The next time priorities shift, meet again with your boss to try to understand the bigger picture.

This could be a great opportunity to demonstrate your strategic interest and desire to understand things at a higher level. You’ll put yourself in a better position to make recommendations instead of executing changes for change sake.

For the boss who doesn’t give helpful feedback:

Jack spent a couple of weeks on a proposal for improving quality, and when it was finally done, he clicked Send to run it up the chain. A week has gone by, so he approaches his leader, Jill, on whether she has any input, or received feedback from the executive team on the proposal. Did she even look at it yet?

A lack of feedback can apply to a project you’re working on, or your overall performance. We covered this in a previous post, but if your boss typically says, “Looks great. Everything’s great. You’re doing great. Keep doing what you’re doing.” It’s a problem.

Get in front of your boss to ask questions on performance like, “what do you see as areas of improvement,” or “If there were one area of the proposal you’d like to see built out, what would you suggest.” This approach demonstrates an interest on your part to engage in higher level thinking and to more than just execute on requests.

What’s the common theme in all of these examples? Communication. In each scenario, you’re taking the lead to open the lines of communication with your boss to understand direction and set expectations. You’re leading your boss to achieve a shared understanding of roles, responsibilities, and direction. Your boss may be too busy, or too scattered, to get there with you without your help. Thus, the reason leading your boss is important, if not critical.

I’d love to hear from you. What other situations have your run into and what approach did you use to effectively lead your boss?

– Jackie Simon

Five Overused Strengths (that may be perceived as weaknesses)

Poor leadership can easily frustrate well-intended employees.

As your career progresses, the same strengths that prepared you for promotion may not be the same that propel you to a level beyond that. The rules of the game change for strategic or people leadership roles. Alternatively, if you feel stalled in your current position, it may be that you’re overusing your strengths and unintentionally holding yourself back.

Here is a list of the most commonly overused strengths and how your colleagues may actually perceive you:

Your Intention: Attentive to Details

How Others Perceive You: Micromanager

As an individual contributor, you excelled at the details and consistently demonstrated your ability to be on top of everything. As a leader, demonstrating this same strength may result in frustration for those around you and set you up to underdeliver key targets. Allow your team to attend to the details and show that they are on top of their objectives, while you focus on setting the vision and leading your team to reach new heights.

Your Intention: Independent

How Others Perceive You: Unable to Build a Team

You built your reputation as an independent, steadfast, reliable emerging talent. Someone who always delivered, no matter the time constraints or challenge. Now that you lead a team and have more resources available, you’re not viewed as someone who delegates effectively or taps into the expertise of others to deliver results as a team. You often work later and longer than your direct reports and feel that the only way to do something right is to do it yourself. The harsh reality is that you’re unlikely to move to the next level of greater responsibility and a bigger team if you’re not maximizing the resources already available to you.

Your Intention: Confident

How Others Perceive You: Arrogant

The same swagger and confidence you built in your role as individual contributor is now rubbing others the wrong way. Whether in your interactions with internal colleagues or external partners, nobody enjoys working with a know-it-all. Drop the words “I” and “me” from your vocabulary. Dial back giving all the answers to ask questions of those around you. It’s possible you don’t know everything. Your team of experts wants to show you what they know and what they’re capable of, so give them a chance and see what you learn in the meantime.

Your Intention: Effective

How Others Perceive You: Lacking Composure

A swear word here, an email marked as high urgency there, a veiled threat to a vendor, and a fist pound on the conference room table has gotten needed attention in the past, raised awareness and assembled resources to work through pressing issues. Now, you’re seen as someone who struggles with maintaining composure. As a leader, you’re expected to set an example for those around you and demonstrate you can achieve results while maintaining a consistent demeanor. Being effective doesn’t mean bringing attention to yourself, it means bringing attention to the issues and demonstrating an ability to resolve them without creating unnecessary disruption.

Your Intention: Ambitious

How Others Perceive You: Pushy

Ambition was a necessary ingredient to helping you achieve promotion. Without ambition, you won’t reach those higher level positions. However, being overly ambitious may cause others to question your motives and distrust your intent. As a leader, be a people builder not a career builder, and focus on helping those around you positively achieve results and receive accolades. Know that your positive intent will be interpreted accordingly and the cream will naturally rise to the top.

For more on utilizing your strengths while leading successfully through others, be sure to check out: Even Great Leaders Have Room for Improvement and Calling “Shotgun!” Won’t Put You in the Front Seat.

– Jackie Simon

25 Powerful Questions For Your Next One-on-One Meeting

There’s no end to the questions we can ask at work to improve our awareness of the business, get in touch with team and employee satisfaction, and show the people we work with how much we care about them and their contributions. The key to asking powerful questions is to frame them in a way that encourages people to answer openly, honestly, and in detail.  Here’s an example of a powerful question: 1. “How do you feel about ____?” Compare that question to the following close-ended question: 2. “Do you like _____?” The first question encourages dialogue. The response will likely lead to information, which will open the door for more questions, which in turn will provide even more information. The second question can be simply answered with a “yes” or “no”. While you will receive a response to the second question, it will be limited in detail, understanding, and value. Here are 25 powerful questions to ask during your next one-on-one meeting with people on your team.

  1. How are you? (YES!  I mean, how often do we really ask the people we work with how they’re doing?)
  2. What would you like to focus on for this meeting that would be of greatest benefit to you?
  3. What has been on your mind lately?
  4. What are you most concerned about?
  5. What is going well?
  6. What would you like to focus on more often at work?
  7. How satisfied are you with the work you’re doing?
  8. What is an ideal situation for you?
  9. What resources would be most helpful to you?
  10. What would you like to see more of?
  11. What would you like to see less of?
  12. Which of your strengths would you like to use more often at work?
  13. What would you like to accomplish next year?
  14. What’s most important to you right now?
  15. What will be most important to you next year?
  16. What motivates you?
  17. What inspires you?
  18. What are you happiest about right now?
  19. If you could do anything, what would it be?
  20. If you didn’t have to manage _______, how would things be different?
  21. You’re doing a great job  ______.  How has _____ been going for you?
  22. What has your experience with _______ been like?
  23. What have you observed about _______ lately?
  24. What is standing in your way?
  25. How can I support you?

– Jackie Simon

Is leading others right for you?

The 12 Worst PowerPoint Mistakes Litigators Make

(Ask your doctor) if leading others is right for you …

In your current position, you may have debated the merits of remaining an individual contributor versus taking on the role of people leadership. There are strong arguments either way, and I often find people are polarized on the issue. Through my conversations with professionals, here are a few “side effects” they have identified in why they’d prefer to not lead teams. They:

  • feel it may be a hassle
  • would no longer just be responsible for numero uno
  • believe they’ll lose work-life balance
  • would miss the opportunity to be an innovator in their role
  • couldn’t imagine not doing the fun work — creating, designing, dreaming, and developing

This sounds like a pretty solid list of reasons to me. For those who have the people leadership bug, here’s a short list of “symptoms” associated with overseeing a team:

  • Leading people means leadership
  • More money
  • More influence
  • Title
  • Greater responsibility
  • Clearer career path
  • Upward mobility

Another great list of reasons. So, when it comes to leading a team versus remaining an individual contributor, what’s the best prescription for career growth? In short, there’s really no right or wrong answer. There are, however, three key things I’d like you to consider:

  1. You don’t have to manage people to be a leader.
  2. You also don’t have to manage people for the greatest gains in compensation, influence, title, and career progression. It’s about creating or finding the right role.
  3. Your decision is only problematic if you’re denying yourself what you really want or you haven’t taken the time to truly explore and understand which direction will best fit you.

If you’ve viewed people leadership as a possibility but have shied away from it up until now, there are many ways you can ease into it (mentoring, pairing, leading meetings, leading teams without the direct reporting responsibility) to build your confidence before you take the plunge. There’s something to be said for having it happen organically.

And, if you’re curious about achieving greatness as an individual contributor, network internally and externally to learn how you can truly maximize your path.

Get really clear on how you envision your career evolving, then go for it!

Next up: 3 Surefire Strategies to Get Ahead

– 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

I’ll Be There For Youuuuu: Making the Move from Peer to Leader

Transitioning from peer to leader is one of the most challenging moves you’ll make in your career.


Here are some of the reasons:

From Your Colleagues’ Point of View:

  • They were accustomed to you as a friend, confidant, and advisor. Given your promotion, they are concerned about how that may play into your evaluation of them as your direct reports.
  • They enjoyed working with your previous boss and may miss that reporting relationship; or
  • Their previous boss may not have been a strong leader and now they’re concerned history may repeat itself with you (fair assessment or not).
  • They, too, may have had their eye on the promotion prize but didn’t receive it for any number of reasons.

From Your Point of View:

  • You feel as though your peer and friendship circle disappeared overnight. After all, how do you remain close friends with people you now lead?
  • You feel as though you were thrown into new territory without a frame of reference. You’re completely out of your comfort zone and feel like a fish out of water.
  • You wonder if you have what it takes (you do).
  • You’re nervous and scared to be at this new level with leaders you once looked up to.
  • You have major responsibilities now. Before you were responsible for just you. Now you must drive a team of people to meet important metrics including revenue, profit, customer satisfaction, production, and quality. And, you must answer to other leaders about your progress.
  • You’re presenting in meetings now, pitching your ideas, and advocating your recommendations to a group of leaders. Sometimes, you’re the only one who supports your ideas. Getting group buy-in is nerve wracking and scary.
  • You’re not sure the people who report to you will like you as much as they did their previous boss.
  • Maybe it’s even more obvious than that. Maybe you’ve received feedback that your direct reports don’t like you as much as their previous leader. While it’s a tough pill to swallow, it’s often the case in the early days of a new leader’s tenure.

If you’re a new leader and you recognize any of the scenarios above, take heart. It’s all part of the journey. It does get better. And easier.

Here’s what to do:

First, be aware of some typical derailing behaviors that many new leaders exhibit:

  • Overmanaging/micromanaging people on their team
  • Failing to delegate projects or tasks, resulting in untimely delivery
  • Failing to staff projects effectively, resulting in their own and team member burnout
  • Failure to build a team, thereby under appreciating and under acknowledging people on their team
  • Being defensive to others about their own and/or team members’ performance

Second, seek feedback from your boss, your new peers, and your team. Forming relationships among your new peer level will help you to move through the transition with more ease while building a new friend base you can speak openly with.

Leadership 360° Assessments are a great way to gather feedback about your leadership performance. They are a well‐known method for gathering feedback from members of an individual’s immediate work circle and measuring a manager’s style and effectiveness as a leader. The 360° method allows key associates to tell managers what they are doing right and what they can do even better. The Leadership Survey is both a powerful performance evaluation and a challenging development experience for leaders. [More on this feedback tool here.]

Third, give yourself time to build a powerful plan. Acclimate over a period of time to your new responsibilities and make observations about the team, work, and what needs to improve and change. At the 90-day mark, that’s generally when the going gets tough. Not only will you be expected to take things to the next level in your new job, but you’ll likely still be juggling some responsibilities from your previous role.

For even more advice on making a successful transition to leadership, take a look at a previous post.

How about you? How did you successfully manage the transition from peer to leader?

Next week, let’s take a look at the importance of etiquette in leadership. We’re all guilty of forgetting our manners from time to time. As leaders though, we must bring our best self to the table every day.

– Jackie Simon

Leading a Leader

To the Exceptional Performer:

Congrats on an exceptional review! Whether it’s for a job well done or teeing up a future promotion or salary increase, there’s a lot to celebrate. After you grab that pat-yourself-on-the-back cocktail, let’s dive in to the work ahead.

An exceptional review likely signals there’s more opportunity for you and greater contributions you could make within the organization.

With any performance review, no matter the rating, a few key points still stand for you to consider:

  • First, look for the feedback themes. For example, are there improvements in overall communication you can make? Is there more leadership you could take within your current role? How about strategic big-picture thinking? Where’s the opportunity?
  • Think about where you’d like to head within the organization or in your career. Do you aspire to lead a team and haven’t yet? Would you like to spearhead a key project or initiative within the company? Do you want to tack “Director” or “VP” on to your title? Think about what’s most important to you.

Once you’ve considered the points above, what’s your plan? Put together a few measurable actions to help you to make those improvements, share your thoughts with your boss, and work together to make those agreed-upon goals your focus for the upcoming six months.

As part of the conversation with your boss, discuss what’s next for you and where she/he sees you heading in the next 6-12 months. Be proactive about this conversation and subsequent follow ups, so you have a clear picture of what opportunities may be on the horizon. This ongoing conversation will help you to evaluate the possibilities ahead, the potential timing, and whether it aligns with your career and salary aspirations.

While your company and boss are important factors in your career growth, the person who will ultimately get you where you want to go is you.

To the Leader:

If you have one or more exceptional performers on your team, it sounds like you’re already doing a lot of great things to facilitate their growth. Exceptional performers seek challenge along with significant professional and salary gains. Top performers can feel stagnant in their growth rather quickly. They prefer not to rest too long on their accomplishments and instead seek out significant responsibilities to progress as quickly as possible. At the point they may see a slowdown in their growth or salary trajectory, they begin to seek opportunity elsewhere – or at least leave themselves open to recruitment. Retention then may become an issue.

With your top performers, here are a few thoughts to help facilitate their growth:

  • First, develop a real action plan with your top performers to help them make improvements in the areas you identified with them. Partner with them to improve upon some key development areas and help them put more of their strengths to work.
  • Evaluate where you are headed next. Do you see a promotion in your own future? If so, succession planning is key here. Identify the individual(s) on your team who you see as likely successors to you and begin delegating key responsibilities of your own to them. Even if your own movement isn’t on the immediate horizon, give your top performers key projects and initiatives to lead and then provide them with feedback on their performance along the way.

Worried about what that will leave you to do if members of your team are doing your work? No worries. It’ll give you more time to focus on your own development and time to coach and lead your team.

  • Invite your top performers to key meetings they may not have access to. Give them opportunity to participate in dialogue they otherwise wouldn’t. This will help to expand their perspective while providing you with feedback and insights you wouldn’t receive otherwise.
  • Make professional development a key one-on-one topic with your top performers. Even if a promotion isn’t likely for them in the next six to twelve months, knowing that you’ve partnered with them and regularly talk about their development is an important retention measure. This regular dialogue opens a door and builds further trust with your team members. Should they decide it’s time to move on to a new position, you’re less likely to be blindsided and more likely to participate in a conversation about their decision.

So, what do you think? Feel free to reach out and share your thoughts and questions.

Next week, we’ll take a look at the question many of us (including The Clash) struggle with at some point in our career: “Should I Stay or Should I Go?”

File:Should I Stay or Should I Go UK.jpg

– Jackie Simon