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

Leading your Boss is More Important than Leading your Team

Image result for manage your boss

Mike: “Jackie, I’m completely overwhelmed and feel as though I’ve really accomplished nothing in the past week. My team seems to over-rely on me and it makes it difficult to focus on my own projects. Whenever I finally have a great idea to help get me out of the weeds, my boss says no.

Jackie: “Tell me more.

Mike: “For example, I have a great idea to bring on a new member to my team to focus specifically on purchasing. I think by focusing the role to one dedicated person, we can create efficiencies and save the company money. I presented the idea to my boss but he dismissed it, saying we don’t have the budget.

Jackie: “What did you do next?

Mike: “Well, nothing so far. Since I can’t get approval to hire, it looks like I have to figure out how to make time to handle purchasing myself. I swear, my boss expects me to do it all.”

Does this dialogue sound familiar to you?

A lot is written about the importance of leading your team, while little is written about the importance of leading your boss. We view our boss as the individual we work for and therefore rely on him or her to make the final decisions, approve direction and clear the obstacles. While we may do the heavy lifting, we ultimately put everything in our boss’s court to resolve and decide. Essentially, we disempower ourselves by believing our boss is the only one with the final say.

If you approach your boss with the understanding that you work for him or her, you’re likely missing the big picture. Arguably, your boss is a member of your team and in many ways, the most important person on your team who you must lead and influence daily. It’s not up to your boss to make the big decisions and clear the obstacles. It’s up to you.

To be most effective, you must lead your boss. And, believe it or not, your boss wants you to lead him or her. I’ll say it again: your boss wants you to take the lead. Meaning, he wants you to make his job easier by lining up the facts, making the business case, recommending the direction, and making the decision. Your boss wants to spend only 5 minutes weighing in on an important issue, not five hours figuring out the pros and cons on her own based on what little information you may have provided so he can make the decision.

You may not be leading your boss effectively if you feel:

  • your boss says “no” to you more than “yes”
  • you can’t seem to get on her calendar
  • decisions have stalled to a halt
  • your boss gets the small things out of the way first; e.g., the things you sent to him only as an FYI
  • frustrated that you seem to have to run everything through your boss
  • you could be so much more efficient if only your boss would respond to your emails

If you feel you’ve been waiting a long time for your boss to get back to you, you’re going to continue to wait a long time. So, change your approach. It’s time to lead your boss.

Let’s say you want to grow your team but you haven’t received approval from your boss to hire someone new to add to your team. Why stop at “no” or even radio silence? How about putting together a plan for your team structure and a description of the role you want to hire for. Paint the bigger picture for your boss and make it easier for him or her to decide. Don’t just stop because your boss said “no.” Change his or her mind.

By leading your boss, not only will you find that your job becomes much easier, you’ll also find you’re getting things done much faster. Not to mention, you’ll be positioning yourself for promotion in the process because you’ll be showcasing your adeptness to lead, manage, take on greater responsibility and get things done.

– 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

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

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

Ten Things Your Boss is too Busy to Tell You

You’ve heard from your boss that you’re doing a great job – and that’s probably the truth. But, if your boss had a little more time to sit down with you and talk about the difference-making steps you could take that would get you to the next level, what might he or she say? Here’s a possible list:

1. You’re doing a great job, but you’re too focused on task-based activities. I’d like to see you bring people development and service/product strategy forward. I want to see that more than your ability to manage the day-to-day. What’s your plan?

2. I don’t see a clear succession plan for you. Who are you developing as your next leader/successor?

3.a. You’ve been in this role for 2 years. I’d hate to lose you, but it’s nearly time for you to leave this group for the next step in your leadership and career growth. Where would you like to head next?


3.b. You haven’t moved to the next role because I really need you in this job. I don’t plan to move you forward anytime soon…unless you bring the topic up.

4. Outside perspective is extremely useful to generate ideas and make changes. Stay open to external resources. Don’t get held back by tunnel vision. What external resources are you reading? What classes, presentations, or conferences do you want to attend? Come pitch me on the investment.

5. You haven’t taken a vacation in a while. Take a 3-day weekend at least every 6 weeks and wait no longer than 3 months for a 5-day break.

6. I know you think you can “fix” team member [insert name], but they aren’t the right fit. You should have had them on an exit plan a while ago.

7. There’s a big difference in the level of contributions of a manager compared to a director compared to that of a vice president. There’s a lot more that I need to see from you in the form of strategy and innovation to recommend that you receive a promotion. But, these are also areas that I won’t coach you in. The next step is yours to navigate.

8. Your team is comprised of the colleagues at your peer level. They are just as important to lead as the team you’re directly responsible for. I’m waiting for a leader to emerge among this group … your move.

9. Your salary increase will be 3-8%…until you pitch me for more.

10. At some point, I’ll be moving on. You could be my successor, but we won’t know until you make your interest known.

Could any of these discussion points apply to you? If so, take this week to think about how you plan to raise the topic for discussion with your boss.

Next week, we’ll talk about the pros and cons of remaining an individual contributor compared to leading and managing a team.

– Jackie Simon