How to say no to the boss

10 tips to navigate C-suite expectations while leading strategic workplace initiatives

by Steve Monaco — May 2019 — In a perfect world, we would be given assignments with clear direction, plenty of time to plan and execute, and zero conflicts between different company stakeholders.  Until then, facility managers and real estate professionals will need to dig into their bag of tricks to create clarity from ambiguity and gain consensus where most critical.  What follows are my top 10 tips and tricks for managing complex assignments that will have people praising you as a magician, juggler and master mediator!

#1.  Don’t say no

Despite what the headline of this article reads, it’s not a good idea to say “no” to your boss.  Instead, try using the phrase, “yes, but…”.  I learned the ‘yes, but’ reply when I worked for Google as a global real estate and facility leader.  Often, when we are given an impossible mission, we immediately start counting the numerous challenges, pitfalls and risks both professionally and personally.  But that’s obviously not what the boss wants to hear.  By reframing your initial response as a “yes, but…” you can convey your understanding of the problem, recognize potential roadblocks, and set the course to navigate future challenges.

Your role is to create confidence through due diligence.

#2.  Schedule your return trip

Early in my career, attending meetings with the company’s top executives was intimidating.  My mind would be flooded with thoughts or frozen with fear of saying the wrong thing.  I’d simply take orders without asking questions or challenging assumptions, usually leaving the meeting without setting expectations.

Today, I ask two golden questions: “After an initial review of this assignment, I’d like to follow-up with questions, concerns, and a planning roadmap; should I contact you directly or with someone on your team?” and “When would you like the first progress update?”  Equipped with these answers, you have now left the proverbial door open for a ‘yes, but’ discussion later.

#3.  Check your motives

If your immediate reaction to a new and challenging assignment is to build a wall and recite (using your inner voice) all the reasons why failure is imminent, then perhaps a self-examination is in order.  Be aware of personal biases and personality conflicts.  Take time to make sure you are thinking and acting objectively despite any difficulties you may have encountered in the past.  Recognize that people have to deploy new initiatives without having the full details or may not be able to disclose certain information for reasons of confidentiality.  A positive mindset is effective and infectious.  Be ready to use it and share it often!

#4.  Find the influencers

Leaders always have trusted advisors.  Your mission is to find out who they are and leverage them at critical milestones.  Whenever I find myself in a situation where I’m uncomfortable engaging with C-suite executive with a reputation for being abrasive, I turn to the people they rely on most.  Administrative assistants are often a big help in this regard.  They may be willing to share their own strategies and direct you to some additional trusted advisors of the executive.

Next, set up an introduction meeting with the trusted advisor/influencer where you can quickly share challenges and ask for advice on how to successfully engage and present information back to the executive.  Chances are they will share their mistakes and help guide you on a direct path to a healthy and productive relationship.

If scheduling a meeting with the executive is difficult, leverage the influencer to get your topic on the agenda at the executive’s next staff meeting.   They were in your shoes once and have risen to the rank of trusted advisor for a reason – because they know how to influence those around and above themselves.

#5.  The dual customer trap

I expect that you have eyes, ears, and hands.  I also expect that you will use them to watch, listen and meet with two different types of stakeholders during an important workplace related change initiative.  When I was at Motorola, I spearheaded a 3,000-person move to our new HQ in Chicago.  As the face of the relocation, my team’s responsibility was to bridge the gap between executing the corporate strategy and making sure the employees were primed for success in a new environment.  If not orchestrated correctly, my team would fall into the trap of catering to one group of stakeholders and ignoring the other.  The secret to avoid this trap is unilateral transparency.

When equipped with the power to influence others, it is imperative to share the risks, roadblocks, and concerns of both employees and corporate executives to each party.  An open dialog and a continuous feedback loop such as FAQ portals, emails for suggestions, and town hall meetings are only a few ways to balance the bi-directional communication plan.

#6.  Test the waters

I love a good surprise when it’s my birthday or an important anniversary; otherwise witnessing unexpected outcomes can be memorable for all the wrong reasons.  A practical course of action to gauge future success of any new initiative is to discuss the idea with others.  Now that you have a group of company influencers (Step #4 above), it’s time to leverage their experience and insights.  Find out what concerns they expect to hear from their respective direct reports, peers and leadership.  If the new workplace initiative is inevitable, such as an unassigned desk policy, then consider inviting a small group of employees to participate in a test pilot program.  During a recent consulting assignment with a tech company, the facility team discovered that people’s perception of the new workplace environment was overwhelmingly better than expected.

Pilot programs can produce powerful testimonials which can trump even the most carefully crafted corporate memo.  The peer to peer review can be a powerful and authentic test sample that employees will remember and share.  Small wins lead to big victories!

#7.  Twitter mentality

C-suite communications should be short and to the point.  Pay attention to the order of how information is written whether it’s an email, presentation or conversation.  Avoid a long opening monologue with mountains of details and extensive background information. If you force the reader to wait until the end of the message to discover the request, you risk that they will not respond at all.  Instead, state your request first with an exact time of when the response is needed (don’t be shy) and then the background information.  Similar to a news article, a great headline will catch the reader’s attention, then a small recap, followed by the details.

I can remember the ‘ah-ha moment’ when one of my mentors shared his advice called the Twitter mentality.  If you only had 140 characters to send a message and your life depended on someone reading and responding, what would you write?  A week later I sent him an email with the subject line, “Need help before EOB – opportunity to save $$$.”

That was 48 characters long (including spaces).  He responded with, “4:30 my office”

#8.  You are the expert advisor

Often, the hardest person to convince that you are the expert is you.

Whether today is your first day on the job or if you’re celebrating a 25-year anniversary at the company, adopt the mindset that you are the expert at finding the answers. One of my most valuable tips for facility professionals when you don’t know the answer to a question is to say, “I don’t know the answer, but I can find it and follow-up in 24 hours.”  Notice that I didn’t say that I would have the answer in 24 hours, just that I’d follow-up in that time period.  Most people want immediate follow-up verses immediate answers.

Many facility related initiatives require research, investigation and references to benchmarks and best practices.  Expect to watch your career thrive exponentially if you’re connected to a greater community of professionals who have deep resources such as the International Facility Management Association (IFMA), Workplace Evolutionaries and CoreNet Global.  In my consulting practice, I am consistently faced with challenging situations and have a proven track-record of hunting down solutions due to my growing network of experts.

#9.  It’s OK to be wrong

If you have checked your biases (#3), checked-in with the influencers (#4), and tested the waters with best practices (#6 and #8), it is still possible to find yourself on the wrong side of the solution.  Priorities shift, key people leave, deliverables are missed, and mistakes happen.  It happens to all of us – even the best.  How you handle the mistake or setback is a character trait that will define you and how senior leaders will remember you.

One of my pet peeves is when someone consistently says sorry as a conversation filler, when in fact they have not done anything wrong.  In my opinion, this erodes one’s credibility, authority and professionalism.  After making a mistake, I believe the appropriate response incorporates transparency, accountability and learning.  Make sure to avoid the temptation to add spin, blame shifting, or diversion through frivolous details.  The only wrong-doing that can really hurt you is not learning from your mistakes and growing in character as a result.

#10.  Be “CRE:ATIVE”

Shortly after successfully moving Motorola to the new HQ in Chicago, I was asked to share my change management lessons learned to a group of real estate and facility professionals at the annual WORKTECH conference in San Francisco.  After considering the common threads of the overall experience, I shared stories about five leadership qualities under the Acronym CRE:ATIVE which stands for Corporate Real Estate: Advocate, Transparent, Inspire, Vision, Engage.  You can watch the 22-minute TED talk-inspired speech here with many more examples of how to navigate a complex workplace initiative.

Final thoughts

Warning!  These tips and suggestions are not a one-size-fits-all solution. Rather they are offered as ingredients to create your own recipe for dealing with the wide range of personalities and relationships you will encounter in the course of your career. If you are a third-party consultant or an outsourced provider, expect that these tips and tricks may require additional effort depending on the corporate culture.

Congratulations to everyone who are already putting these strategies into practice.  An even higher praise is awarded to those who are teaching the people you manage how to say “yes, but” when in a meeting with you.  As the author of your career, make sure to challenge yourself to listen carefully, communicate clearly, and grow exponentially.

Author Bio

Steve Monaco is a corporate real estate and facility consultant with over 20 years global experience leading high-performance teams for companies such as Google, Motorola, and Lenovo. Providing executive-level expertise, Monaco & Company manages complex program initiatives for the entire lifecycle of a transaction including leasing advisory, design and construction, change management, and post-move experiences.

Steve has been awarded IFMA’s Global Award of Excellence and Project of the Year from CoreNet Global. His broad experience as a broker, architect, general contractor and property manager has equipped Steve to negotiate from every side of the virtual table. For more information visit

Workplace Evolutionaries’ (WE’s) mission is to “change the world one workplace at a time.” It’s a global community of over a thousand professionals who care deeply about the world of work and where it’s going. Among its members are workplace strategists, change managers, facilities managers, architects, designers, HR professionals, IT managers, academics, and product and service providers. WE members enjoy three conferences a year, monthly WEbinars with thought leaders from around the world, a monthly round-up of the best workplace research and news, white papers, and a vehicle for connecting with fellow evolutionaries around the world. WE is a global Community of Practice within the International Facility Management Association.