How to Juggle 2 Bosses and Make It Work for You


What’s harder than pleasing your boss? Trying to please two! Relationships with leaders are core to your current and future career, so you’re smart to focus on making them work. Until recently, I’ve written and coached clients to reframe the boss dynamic to their advantage when there is just one boss, as in my article Imperfect Boss? Perfect Opportunity.

Dual reporting has been on the rise as organizations cease to replace positions and C-level executives take a more hands-on approach.

Joann Lublin recently addressed the realities and challenges of this scenario this in the Wall Street Journal . In her article, Brian Kropp of Gartner affirms “We expect the number of employees with multiple managers will increase based on organizational needs tied to the ‘new normal’ of people working from home.”

Ms. Lublin asked me to comment on the challenges and benefits of these arrangements:

“Conflicting time allocation, deadlines and performance targets can lead to your disappointing both bosses—and negatively affecting your career,” warns Stefanie Smith, a management consultant and executive coach. She has counseled dozens of executives with more than one boss during the past decade, and seen such clients increase since the pandemic hit. Ms. Smith urges them to create a shared vision for their bosses, “much as our eyes work together.”

During the interview, I addressed some other questions and would like to share my thoughts and tips with you.

How has working virtually during the pandemic made it harder to have multiple bosses?

The current shift to a dramatically more virtual work environment has led to:

  • Decreased natural chances for informal exchanges or brainstorming sessions between you and each of your bosses, or even three-way conversations. In the past, these may have taken place impromptu or before or after another meeting.
  • Higher pressure plus greater distractions arising from health concerns, life disruptions, travel limitations and working from home. Everyone’s adjusting to being farther away from their teams, having children at home (and new office) or an unexpected separation from aging parents.
  • Loss of the casual back and forth, creative energy and relaxed ease that takes place face-to-face, whether over lunch, coffee or dropping by someone’s office. Videoconferencing does not typically include or support body language, “walking and talking” or spontaneity of expression – all vital components of interpersonal communication. As a Director at Anheuser-Busch commented “You can’t read the room anymore, because there is no room to read!”

Are there professional benefits of reporting to two bosses?

Yes. You gain twice the access to senior-level perspectives, mentorship and networking. Plus, you gain exposure to strategic business drivers across multiple functions or groups. The more you combine the expertise and energy of various teams, the more you:

  • Enhance your reputation and visibility within your organization as more people are involved in and aware of your initiatives.
  • Amplify the business impact of your ideas, which also advances your team.
  • Expand your sphere of recognition and influence beyond your organization as you are involved in discussions, events and forums on multiple topics.

For example, as Director of Talent Acquisition, you may be hearing the CEO’s directives at the same time you are hearing professional development or performance management challenges from a business unit leader you report to as well. You might combine these perspectives to develop an initiative across the company to identify skill sets required for stronger market positioning and then propose innovative recruiting tactics to attain them. If your ideas are implemented, you reap twofold rewards.

Reporting to two bosses can be uncomfortable, no doubt. You can manage it though, and come out ahead. One of my clients heads Digital Marketing and reports to the CIO and to the CEO at a growing company that designs apps and promotes VIP events for music artists and their fans. Rachel identified an opportunity to invest in an e-commerce platform upgrade which would enable greater volumes and more efficient SEO campaigns. The CIO is driven by technology enhancements, yet while the CEO aims to expand online revenue, he is also concerned about keeping costs down for the next quarter during these uncertain economic times. She knew she would have to balance the interests of both bosses, while being as responsive as possible. When she first made her pitch to hire a freelance programming expert on a short-term basis – there was hesitation.

One solution I encouraged, and reinforced when her work went fully virtual overnight, was to write a combined weekly update encapsulating accomplishments, project status and proposed recommendations with succinct rationales explaining the benefits in language that would resonate with both leaders.

This led to an open dialogue which made it clear that a minimal investment would yield substantial returns for the company and their clients, even in the short term. They went forward with her recommendation, which has already paid off.

A friend who reports to two partners in different departments of the same firm recounted to me a day when he was working all out to finalize a memo for the client of one partner. At midday, the other partner called him requesting immediate research on a prospective deal announcing, “I need this by 5!” as he walked out of the office with his golf clubs. My friend responded, “Is 5 am OK?”

If these situations feel familiar and perhaps you’re feeling the strain, let’s look at strategies which will enable you to thrive

Aim for clarity and convergence

The benefit of having two eyes is that they have different angles. Visual convergence enables depth perception so we have a much clearer picture of what we see, In the same way our eyes work together to provide a stereoscopic image, viewing your organization from two angles will provide a deeper, clearer understanding of what it takes to succeed and how you are part of that success.

Ensure both bosses are completely clear on major project milestones, performance targets, deadlines and resource requirements across both roles. At the same time, you want to embrace both of their perspectives. With that shared vision, you can converge your schedule and focus to achieve on both fronts – as an individual or as a leader of your own team.

“Align and combine” metrics and goals

Your performance goals for each leader, should complement each other, or at the very least not conflict! This will provide a consistent framework for making decisions about timing, resource allocation and sequencing of work.

Go for the “Win-Win-Win”

Try to find ways your two reporting hats create extra value on both sides and for you. Another client is the CEO of a subsidiary of a multinational medical products manufacturer. He reports up to two executives at the global parent company. The EVP of Product Development aims to expand market share of innovative new offerings. Meanwhile, the SVP of Sales evaluates performance on added margin regardless of product line and channel. Different goals. We looked at ways to could encourage effective exchanges of data and ideas to increase both profitability and market share, which boosted his rapport with both leaders. Be the bridge between your bosses, so it’s not a zero sum game, but rather the sum is greater than the parts.

Deliver regular updates to both bosses

Report each week or month on progress across both roles, including accomplishments by those on your team. If possible, follow up with a phone call with each of them. If it is not viable to share the same report with both executives, think of a way you can write a separate section to include both. As demonstrated in the example above, a joint update enables both leaders to see how your time, energy and talent are being directed, whether you are shifting between two sets of priorities, or dividing your time in a way that keeps them distinct. It also provides a record of achievements for future reference.

Keep the dialog WIDE open

…in terms of both frequency and volume. Find a way for both leaders to communicate with you and with each other if there is an urgent or unexpected need arises. Avoid being in the position of deciding how to balance work if for example, one wants you to complete a highly visible strategic plan, while the other needs you to put out a fire just called in from a prominent client.

Do not wait for a semi-annual or annual performance review. With two bosses, the chances of misunderstanding, envy and competition are a greater risk. So take responsibility for asking “How am I doing and what could I do better?” regularly, when all is calm and all is well. This is the time you have the bandwidth to think big picture about how this can work – not when you’re running fire drills.

Reporting to two bosses can double your trouble – or your opportunities. If you deal deftly, you can gain increased professional recognition, influence and collaboration.

Go for your own Win-Win-Win! Let me know how it goes.

Job Change for Professional Growth? 5 Factors to Consider

job-change-for-professional-growthIs the chorus of the classic hit “Should I Stay or Should I Go?” by Clash running through your mind? Questions about job changing are top of mind for many as reflected in Joann Lublin’s recent article “Job-Hopping Executives No Longer Pay Penalty” in the Wall Street Journal.

When Joann interviewed me on this topic, her opening question was “Is there now less stigma attached to job hopping since it’s so rampant among millennials?”

My response – while job hopping has traditionally been seen as a red flag by prospective employers, they are now more open to hiring candidates who have recently changed jobs due to several trends:

  • Online recruiting: candidates are much more quickly and easily identified and targeted by recruiters and companies. This means changes may be viewed as a response to a great opportunity rather than an impetuous action. Several of my clients have been contacted soon after we update their LinkedIn profile with their new job information.
  • Organizational decisions unrelated to performance: corporate restructuring, outsourcing or relocation. All are easily verified by hiring managers. Some people move due to the reality of losing their jobs due to these events, others move in anticipation of them.
  • M&A or a private equity business integration: When companies merge, they may eliminate dozens of jobs without any deep analysis.

In all of these situations, job change is easily explained and not premeditated.

While not the right choice for everyone at every moment, I’ve worked with clients at all phases of their careers who have changed jobs in fewer than three years, made successful transitions and are pleased with their choices. Below, I offer some of the advice and questions we explore when making the decision to make a career move soon after a previous change.

5 Questions Before Making Your Move

Your career advancement decision may not be easy, so let’s think it through:

1. Is the timing better today, or are you better off bolstering your potential and setting the groundwork for a move six to twelve months out?

Lack of demonstrated promotions or advancement within an organization, may lead to doubts by future leaders about the wisdom of investing in your professional development. On the other hand, you may want or need to make a quick move to avoid a problem that is brewing.

Here’s an example. An Accounting Director with decades of experience lost his job of 14 years, along with 400 other people who were “restructured out” the same day. After intensive coaching discussions, working through my ebook program, and then interviewing he attained a position at a thriving financial firm, with more responsibility and more upside than he had before. He was even promoted within months, practically unheard of in a privately-held company. Sounds great, right? Well only 11 months later, that company decided to move their operations to another state. Relocating was simply not an option for him due to family obligations. After we reviewed carefully together, he decided to start looking proactively before the operational move took place – a tough choice because there were financial incentives to stay. His new search landed him in a new position as Controller, thus achieving his five-year objective within only two years!

2. How does your work history provide an advantage in the specific role and organization you are considering, and how can you speak directly to it?

Hiring leaders may be understandably skeptical and concerned about bringing on a new team member with a history of leaving jobs quickly. From their perspective, what the role requires and the why the candidate moved are critical. Leaders looking for someone to fill a role with a substantial learning curve and desired longevity would prefer a candidate who has demonstrated the ability to roll with the business cycle punches.

In other cases, leaders may need a person who can hit the ground running, adapt quickly to new environments and thrive in changing circumstances. If a professional has successfully moved from one role or organizational culture to another, it may indicate an ability to quickly get a read on the new environment and the leader’s priorities. This could be useful if a business is doing a strategic assessment, or engaged in an M&A or private equity investment.

My friend Adam Weiss, an executive recruiter put it succinctly, “Context is everything. Candidates need to communicate why their resume has a logic to it, not just bouncing around.”

A candidate with multiple recent technology jobs might say to an interviewer: “There are two ways to approach business systems integration: 1.) incrementally with rolling milestones or 2.) extended planning and testing followed by a clean cutover. Over the past three years, I’ve done it both ways, at two different companies, and can work with your team to fully vet the pros and cons of each approach.”

3. How will your reasons for moving influence your reputation with and the impression you make on your current network, hiring interviewers and future colleagues? What are the “optics” and how will you explain your decision?

Will you be seen as a disloyal or a potential personality problem or will you being seen as ambitious and ready to take the next step?

Maybe you moved because a boss moved and took you with her. This indicates loyalty and value. Trading up quickly may also show ambition and talent. Sometimes a situation even combines both decision factors.

Kristin is a graphic designer who is very motivated to excel. A year after graduating and taking her first job with a small design firm, her boss moved to a nationally known firm with bigger clients, and invited her to interview at the new firm. Kaitlin worked through the pros and cons, she interviewed, got an offer and accepted it to attain greater exposure and broader technical skills.

Samir was working for a start-up related to alumni networking, when his alma mater contacted him with a terrific alumni relations opportunity which he accepted. A year and a half later, the organizational landscape changed in a way that limited his options for growth. When a recruiter called him suggesting a focused search, he pursued it and landed a leadership role at a leading European university. Now at 29, Sam has reached his goal of rising from staff to management and taken his game to the next level. His decision path is clearly understandable and the results impressive.

If you aren’t convinced, you won’t be convincing. Your logic and the way you communicate it will influence how people react, so spend the time in thinking it through, getting outside advice and practicing until you sound, and really are confident and certain.

4. What will you in gain career and financial advancement by moving versus staying across these factors:

  • Financial benefits: salary, bonus, incentives or options based on longer-term success or tenure (’nuff said).
  • Job promotion and professional growth: Where will you achieve your current objectives in terms of industry, type of company, or focusing on more exciting and marketable capabilities? You may want to move to shift from a general HR role to becoming a training specialist, or from being an Accounting Director to running the IT aspects of M&A integration or transitioning from consulting to a corporate leadership role.
  • Credentials or project leadership quals: There is a reputational and emotional risk to walking away before leaving a positive lasting impact. You may want to follow through on initiatives you started to own the results or impact of the work. When you apply your knowledge to advancing others, you often elevate your own position and influence as a result.
  • Status and culture of the organization or company.
  • Opportunities to network and establish connections with colleagues, clients and strategic partners.
  • Learning from your current or potential new boss or mentor.

5. What will you gain personally by moving versus staying? Consider these 3 factors:

  • Job security and satisfaction: Emotions and practical realities are important. Do you feel an ease and sense of alignment where you work now? If you’ve recently lost your job, where will you feel more secure? If you’ve been in a job for years and have enough saved for retirement, will it feel great to have a fresh start?
  • Non-financial benefits: What matters to you and what is available? Tuition reimbursement, superior healthcare coverage, corporate perks and activities?
  • Life balance advantages: Achieve a life balance objective – relocating to a more desirable place to live, attaining more flexible hours, or fulfilling a personal value such as improving conditions and opportunities for production workers at a manufacturing facility.

If you carefully take the questions above into account, you’re much more likely to feel solid and secure when answering that important musical question “Should I Stay or Should I Go?” Good luck singing your own career tune!

Stefanie Smith leads Stratex (, an executive consulting and coaching firm based in Manhattan, providing project leadership, customized workshops and coaching programs to advance executives and their teams to the next performance level. Her ebook: The Power of Professional Presence: Get Their Attention and Keep It! is available on, iTunes and

How to Make Your Team Poach Resistant

In the “information age” environment, executive recruiters, corporate HR, hiring leaders, team members incentivized by finder’s fees can search for talent faster than ever. With the powers of LinkedIn and Google, they can identify professionals with the skills and background needed, no matter how specific, or how much in demand those credentials may be. My clients consistently find that only days after we expand their online profiles to include details of their expertise, from “Chinese market development” to “brand expansion” to “palliative care management,” they receive contacts from companies and recruiters seeking their specific qualifications.

In the hot growth sectors, there has been a considerable focus on this trend, as covered in the May 2014 issue of Inc.: How to Master the Art of Poaching Employees.  Naturally, this creates a challenge for leaders who seek to retain their best players, without resorting to the obvious (and not always successful, and not always possible) tactic of increasing salaries. To provide some additional context and guidance beyond my tips included in the article, I’d like to offer the following:

  1. Ask and learn first.
    Express genuine interest in your employees’ career aspirations. Absorb as much detail as you can, before explaining how they can become more valuable to your organization.  Listen attentively to the words they use and the emphasis they place on certain priorities.   By asking open-ended questions, you’ll learn a lot in a short time.  For example, “What would you like to say about your professional role a year from now that you might not be able to say today?”You can also gain clarity on their personal or work-life priorities which as a leader, you may be able to align with higher job satisfaction and motivation. Follow up with a responsive solution. In one case, a Director at a leading financial services firm learned that her marketing manager regretted not participating in his child’s school events. She suggested, “Would it be helpful if we organized your schedule so you could take half a vacation day every other month to attend your son’s concerts or sports practices?” The marketing manager was relieved and appreciative of this simple solution which only improved his loyalty and performance.

2. Understand the breadth and depth of their strengths.
Take time over lunch or during a one-on-one session to review the backgrounds of your colleagues and your team – you’ll be surprised at the information and advantages you may discover.

Let’s say you’ve been thinking about the potential benefit of better business results analysis. Someone on your team, who is a specialist in regulatory compliance today, may have had a prior role in financial reporting. You’ll never make the association if you don’t fully understand that person’s background and skills. On the other hand, maybe you’ll learn that your Travel Manager was an actor for years after college, and could be useful at trade shows, or in certain client-facing situations which require a strong presence and a bit of dramatic effect.

3. Outline a 12-month plan with mutual clarity and commitment.
After you have listened, then you can propose a win-win match between your strategic needs and their professional and personal aspirations.   Have them write up a 12-month professional growth plan for your review. Then agree in advance that you will schedule quarterly checkpoints. Set realistic and achievable goals: the idea is to create win-win momentum, not additional stress or pressure.

4. Remember: they are entitled to feel recognized.
While Shakespeare assures us “that which we call a rose by any other name would smell as sweet” when it comes to job titles, people truly care. Once a year, review each person’s actual contributions and role. If possible, collaborate on a title which accurately reflects his or her contributions, within bounds of what your organization allows. Offering the highest, most descriptive title possible will make people feel proud, connected to their role, and recognized. It will likely work in the company’s best interest as well as customers and vendors will also appreciate the expertise of their contacts.

If you try this out and would like to share the results, or ask any questions, pleasecontact me.

Which Way Should You Lean ?

In response to the widespread publicity on Sheryl Sandberg’s book Lean InMoney Magazine asked me to comment for their counterpoint article Lean Out.  I was quoted as advising that if you seek greater authority or higher pay at your current job, you should ask your boss what it would take to get promoted and, “If there isn’t anything you can do, you should be leaning out.”

Since then, readers, colleagues and clients posed some thoughtful questions, which I would like to share, along with my responses:

If I start to expand my circles or upgrade my online profile, what will my boss and coworkers think?

I understand the natural tendency to worry about the outside reaction to your efforts to advance yourself. Rather than viewing this as a solo act or self-aggrandizing endeavor, engage your boss and coworkers in the process – ask for feedback or time to brainstorm your action plan. Present initiatives tied to strategic goals and market objectives, and discuss how you can capitalize on them together.

If you provide internal training and demonstrate and share the depth and breadth of your knowledge within your organization – it reflects well on your entire department. In one case, when I trained a client to speak with the media and introduced him to an editor at The Wall Street Journal, we also invited the CEO to participate in the interview. Hence, my client became responsible for the CEO’s most prestigious press quote to date, while also gaining the same exposure himself.

Can I lean out while still maintaining my primary focus on my current job?

The Lean Out article shares several excellent examples of professionals who decided to leave corporate roles for options which better suit their values. Is this the only way to lean out? Absolutely not!

In fact, when you start to “lean out”, you also increase your chances for promotion within your current company or potentially at another.  You can “lean out” in ways that are win-win to simultaneously enhance your career and add to your company’s bottom line. There doesn’t have to be any conflict at all (see the next question).

You recommend leaning out, but how exactly can I? What can I do?

Consider three levels of leaning out, all of which benefit you and your organization:

  • Enhance your own professional standing

    “This quarter, I will invest $300 to advance myself by…” Reality check: If you don’t invest in yourself, how can you expect anyone else (including your boss) to invest in you? Maybe it’s time to upgrade your LinkedIn profile with details to properly convey your achievements, such as a customer acquisition milestone or the performance recognition award you received but neglect to mention out of modesty. Or, maybe this is the time to take a course you’ve been thinking about for years, buy an elegant new suit, hire a temp to organize the mounds of files in your office. Do whatever works for you, but make it count!

  • Extend your company presence beyond your immediate group at work:

    “This quarter, I will invite the following 5 people to lunch …” We’ve all heard “It’s not just what you know, it’s who you know.” But beyond that, it’s how well you know them. Seek out those beyond your immediate group at work who can mentor and enrich you – perhaps colleagues with whom you can exchange ideas, and former subordinates who have now gone on to new and higher roles.

  • Expand your industry and media presence:

    “This quarter, I will step out of my comfort zone by…” Maybe you will talk to the press, lead an event in your area of expertise for your alumni group or attend a trade show to make new contacts. It may be a challenge, but you’ll reap the rewards of increased job security and confidence.

If you are interested in accessible, actionable steps along these lines, my ebookThe Power of Professional Presence: Get Their Attention and Keep It! (available onAmazon and iTunes), contains recommendations for kicking your online profile up a notch in Chapter 5, and ways to prepare for and succeed with media interviews in Chapter 6. Please contact me if you have any other questions or comments.

Personalize Your Service: Make Your Business Pop!

Make your business pop! | Personalized service tipsSometimes a product or service has your name on it.  Literally.  It happened to many of us thanks to Coca-Cola’s recent “Share a Coke” marketing campaign. Bottles were printed with various names on them and distributed at random, creating the fun challenge of finding your name or a friend’s name on a bottle.  My friend Stefan, the Maître de Cabine (Cabin Chief) at a major European airline sent me this photo which is untouched and unaltered.

What’s really clever is the clear note of customization, while the product and branding is as consistent, familiar and unique as always.  The value of striking this balance has been on my mind, since a recent interview High-Profile Clients—Worth the Hand-Holding? .   I was quoted on anticipating clients’ needs and news to provide them the maximum value with every conversation and project.

When I showed Stefan the article, he replied, “Exactly.  On my flight today from Chicago to Zurich, I had 229 passengers with 229 different needs.”  His comment made me realize: being the in-flight service manager for overseas flights may be the ultimate intense client relationship situation.  How many of us are within a few steps of our clients for 8 or 9 hours at a time ?!  Intrigued, I asked Stefan how he personalizes service while adhering to all the airline rules and regulations.  His response reflects the high-touch elegance many of us associate with Europe:

“When preparing for a flight, I review the passenger list so I can personally greet our top customers, and maybe chat a little.  The passengers often feel honored that “the man in the uniform” not just only asks “coffee or tea?” but is also informed about them.

We have to find out how people “tick” and what they want most.  After many years, I’ve come to understand and train my staff to recognize:

    • the “gourmet” is on board to eat and to try every single wine, wants to enjoy our in-flight service and wouldn’t mind an 8-hour meal service!
    • the “worker”  looks at a laptop from take-off to landing. Sometimes when you look at the screens, you see they’re actually playing solitaire, but they usually don’t want to be disturbed and are very reserved.
    • the “sleeper” just wants to sleep. They might eat something – however it has to be served (and cleared away) ASAP.
    • the “communicator” needs a lot of attention, rings the bell all the time, has a question every time you walk by and wants to know everything. They also enjoy it very much to talk to the Cabin Chief as they feel it makes them look important.

The skill for us is to find out which category the passengers belong to … because you sure don’t want to talk to a “sleeper” about the weather!  A “worker” sitting next to a “communicator” is a red flag we need to notice.  Of course, there are many other categories and people belong to more than just one category. For example, a combination “gourmet/sleeper” can be challenging!”

Right there, Stefan shows us how to take the concept of market segmentation and put it straight into action.

Now, for those of us down on the ground … how can we better customize our services?  In your work, “customers” might be colleagues in other divisions, contacts at strategic partners, or multiple bosses.  You may not be able to diversify bottle labels, or offer extra legroom, but we can still find out and respond to what different people want most.

Here’s an example from my experience:

An executive client with over 200 people reporting to her and a heavy travel schedule requested I reformat our post-meeting action plans.  She threw down the challenge, “no more than three finger rolls, Stef.”  She meant how many times she had to touch her screen to scroll through the email on her Iphone.  Yet, she always had multiple projects in play at once and it’s my job to capture all cogent points and follow-ups.  Thanks to her, I added color, subsections and weblinks when helpful. I’ve have been using this condensed format with all my clients ever since.  Guess what?  They all love it!

Three questions to kick off your own client customization campaign:

  1. If you were to categorize your clients according to traits and preferences, what would be the three or five meaningful groups?
  2. How could you respond differently to each group, while maintaining consistent product/service quality and branding?
  3. What questions or opinions might you ask to better tailor your communications, reporting or service approach – while maintaining the essence of what makes your business special?

For a strong final quarter of 2013, let’s all keep in mind: It’s not just business, it’s personal!  Please contact me with any examples you’d like to share about how you make your customers feel like your products or service has their name on it.