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

Become an Instant Expert

Want a new challenge? Looking to identify your inherent talents and strengths? Want to be seen as an instant expert? Teach! Spread the word! Share your knowledge!

A great way to challenge yourself, get unstuck, learn something, and elevate yourself is to share your expertise with others. Maybe it’s a Lunch ‘N Learn session. Or an online training course. Maybe you go balls out and become adjunct at a local college. Be a mentor and have regular meetings. No matter the “who” or “how,” try your hand at teaching. When you listen to yourself teach and see the light click with others, you’ll soon realize how far you’ve come and you can better identify your next move.

–  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

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

Should Happens

Shoulding all over yourself. Sounds terrible. Do it too often and your life can really become a mess. “I should ask for a raise,” “I should have prepared better for my speech,” “I know I should go back to school,” “I’ve been told I should start a business.”

How often do you find yourself using the word “should” to describe your “almost behaviors?” How realistic are your expectations?  People hide behind “should” when they don’t feel empowered. What are the true roadblocks you feel are in the way of changing your “should” to “did”?

–  Jackie Simon

Sell it like it is

You may be giving a lot of thought lately to the next step you’d like to take in your career. One that will result in greater responsibility, upward mobility, and increased salary and bonus opportunity.

Have you considered sales?

It’s a question I love to ask people in the process of developing a vision and plan for their careers. Some embrace the idea of sales while others immediately shoot it down. Why is that? I often find it’s because individuals have a preconceived notion of what sales involves and have dismissed it very early on.

Maybe you have dismissed sales as a next step because you believe it’s:

  • Many more instances of “no” than “yes”
  • An unending loop of PowerPoint decks and presentations
  • Travel intensive
  • Tied to weekly/monthly/quarterly sales goals you own and are accountable for hitting

Could there be some merit to these points? Absolutely. Depending on the role, sales can certainly involve all of the above.

But, there so many other facets to sales-like roles within organizations that actually can take a “none of the above” spin to them.

The key reason to consider a stint is sales is to prepare and position you for great opportunities down the road.

Sales teaches professionals to present ideas, position possibilities, motivate thinking, and negotiate outcomes. It teaches individuals to enlist others and get them onboard and turn a no into a yes.

Sales teaches professionals the valuable skill of influence. And, mastering the skill of influence is extremely important to your growth and career development no matter the role you’re in.

Let’s say you want to pitch your senior vice president on a great new product or service idea. Or, you want a promotion to the next level and have great ideas on a position the company could create that you’d be great for. Or, you want to get in front of the CEO of your company because you’d love her to be your mentor. To achieve these things and get attention, you need to influence others within your organization. You need to sell them on the possibilities and benefits.

If working directly with clients and pitching products and services doesn’t sound like a great direction to you, there are still other options. Perhaps you’d enjoy product or technical sales support, product marketing or management, or account/customer service support. Roles like these often involve learning how to position products and services and work with clients to positively influence their experience with the company.

Let’s say you see yourself owning your own business down the road. Mastering sales skills sooner than later will be a tremendously valuable and important skill for you to make your business a success.

If a role change isn’t a possibility for you at this time, here are a few other ideas on ways to learn and build your sales and influence skills:

  • Ask friends or family members who work in sales to teach you some techniques
  • Shadow sales team members within your company
  • Invest in a sales training course or two
  • Read a few books that focus on sales development
  • Follow blog posts and Twitter feeds from sales leaders

Whether it’s taking on a selling or sales support role or expanding your professional development to include sales training, you’re sure to acquire valuable techniques for presenting yourself and your ideas to influence buy-in.

Ultimately, building this skill set will put you on a great path for positions of greater responsibility and compensation.

Next week: Should Happens.

– 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