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.

Leave a reply