Ask a CEO: How Can I Make a Totally Unreasonable Request (When I’m Sure They’ll Resent Me for Even Asking)?

A female CEO we love! Indra Nooyi of PepsiCo.

This is the second in a monthly series in which we ask women CEOs a burning question, and they answer. Be sure to check out the first post in the series if you haven’t already. I’ve been interviewing more than 100 CEOs and exploring the relationships between their success and effective requests. These women all own companies with revenues of 1MM and up. Want to ask a CEO? Email your question to

They’re not feeling it.

You haven’t even asked yet, but you can tell they’re not going to like this.

And you really need to make this request. Whether they’re your staff, family, partners, or business heroes, it would mean everything to have their support.

It seems you have two options.

Option 1: You can stop yourself from making the request in the first place. After all, asking for this would be unreasonable. And even if they say “yes,” what if they spend the rest of their days resenting you for it?

Option 2: You can charge ahead and force yourself (or them) into doing it. This might work once or twice, but force leads to resistance. It’s not a sustainable way to live.

In working with hundreds of leaders and their teams, I’ve noticed that successful women have tapped into a third way.

Option 3: Asking with intention.

What does that mean?

Act as if anything you desire is already here and banish your doubt. When you shake off your doubts, anything is possible. Your intentions determine how quickly and effectively you reach the stars. I believe we all tend to use our thoughts to create the world we choose. If you doubt your ability to create the results you intend, then you are refusing the power of intention.

To ask with intention means you have identified your limiting beliefs and assumptions while freely choosing to believe in that which moves you closer to your finish line. On many occasions, this requires belief without a shred of evidence. My clients are often surprised to discover and identify the beliefs that are holding them back from what they know is possible. Enter Fear. Judgement. Stubborness. Coming to terms with those, gives way to eureka moments that deliver the goods.

Creating clear intentions unleashes bold moves and wild success. I got specifics from CEOs who faced real-life challenges in which they decided to make an unreasonable request–and did so by asking with intention.

Let’s look at 6 situations where you may think you can’t make an unreasonable request—and how these CEOs asked with intention.

1. “I’m the boss—no one else cares about the outcome as much as I do, so I can’t possibly ask my team to go above and beyond.”

“I used to consider myself the boss. At one point it felt powerful–a sort of an ego trip for me. Now I don’t put my title on anything anymore. I have people who have worked for me for years. They are constantly going over and above what they need to do because they feel the company is not just mine, but it’s theirs, and that is the key of success. I’ll share if we are going through challenges. I’ll ask them what can we do better here. It’s a very different way of managing now. I have conversations with them all the time, and on a regular basis, we’ll bring in personal stuff when there’s something going on. Sometimes they’ll say, ‘I don’t want to talk about it,’ and I respect it. I’ll say, ‘Okay, if you need something, let me know.’ Work shouldn’t be just about work—it’s about life. If people are sick or a family member passes, I give them the freedom to take care of their life, and reassure them their job is here. In return, they are so dedicated.”

—Lisa Brazelton, founder of Total Coordination Professionals

“You have to find the ‘win’ for the person you’re asking. You have to paint a picture for them to see how complying with your request is to their benefit. Example: More cold calls = more qualified prospects = more sales = more money for you. Tell them the final result you hope to accomplish, the guidelines they may need to work within (budget constraints, legal, etc.) and then let them chart the path. If you feel they are off-base, then talk about it. Use words such as ‘you might want to,’ or ‘you could.’ Replace the word “should” with “might” or “could.” Give feedback in a positive way. Example: They tell you their plan and you see some pitfalls. Consider saying, ‘Good work, but how would it look if we…’ Personal thank you notes and phone calls, restaurant gift card, tickets to a play, etc. can also help your team realize that you really do appreciate their efforts. Once they realize they are important to the success of the company and that you recognize that, they are more willing to step up, do as requested, and, more importantly, think strategically and come up with ideas of their own that will move the organization forward.”

—Debbie Simpson, President, Multi-Craft

2. “How can I possibly ask my staff to take a pay cut?”

“The hardest thing I have asked for ever was of my staff. They’re world-class, and I’m not just saying that. When the economy turned, I made a conscious decision to not participate in the recession. I spoke with my accountant, and agonized for many nights. I wanted to figure out a way to keep everyone on board. We decided to ask them to work a four-day week, every other week. If people had hardships they couldn’t overcome, I would try to help them in other ways. That is how we managed for one summer, so we could run the company. It was the saddest day and the happiest day when I told them it was going to be over. They got really used to working those four-day weeks! I was so happy we maintained our full staff, and never laid anyone off.”

—Adrienne Giannone, President/CEO of Edge Electronics, Inc.

3. “How can I ask for more compensation from a client or partner who doesn’t have the funds?”

“A woman who owned this company came to me and asked me to consider coming to work for her, even though she couldn’t afford me. I told her I would, on the condition that my lowered salary was earning me a partnership in her business. She agreed, and we became partners. After 10 years, she decided to leave the business. I bought her out, and now own the business myself. In retrospect, I still can’t believe I asked for that. I’m still amazed she agreed to it. We had a very successful partnership. The business grew and expanded, and we worked extremely well together. We both had assets the other lacked, so we made a very good team. I worked more than ever, but also made more money than I ever would have. I am no longer afraid to ask for what I want like I always was before.”

—Carolyn DeNapoli, Owner, Direct Sign Systems

4. How can I ask for a reduced price from my vendors?

“Although I do not like to ask, it is very important that you do ask for a reduced price from your vendors. Many times prices have gone down or competitors’ prices are significantly lower, and your vendors will not pass along the cost savings until you request it. I always have to ask my employees, “Did you get it in writing?’. I am sure they will write ‘Did you get it in writing?’ on my tombstone.”

—Adrienne Giannone, President/CEO of Edge Electronics, Inc.

“From my vendor partners, I’ve asked for their help in keeping costs as competitive as possible so we could secure and maintain business with clients. I’ve also asked them for their best service, so together, we provided the best service to the ultimate client.”

—Joan K. Bradley, PharmD, President/CEO, The JB Ashtin Group, Inc.

5. How can I ask my partner for more help at home?

“We realized early on in our marriage that my passion for my business was greater than my husband’s passion in his career, so we agreed that I would focus on mine and he would focus on everything at home. So when I came home from work, I could devote my time and focus on our family, and not have to worry about groceries, laundry, bills, or other chores. This was not as easy as it sounds. A lot of frustration (both of us) and tears (mine, not his) came and went before we agreed on how to move ahead. Knowing what both of us was responsible for took away much of the everyday stress of working and raising children. My husband and I have a wonderful partnership that has lasted 25 years so far and our kids (now 24 and 18) still really like us (smile) and are successful in their own lives.”

—Joan K. Bradley, PharmD, President/CEO, The JB Ashtin Group, Inc.

6. How can I ask for a mentorship from someone who doesn’t even know I exist?

“When I first opened my business, the thing I needed most and asked for often was guidance. I reached out to every successful person I knew and asked them to spend 30 minutes with me. I respected them so much and appreciated their time, so I made sure I came prepared with a list of topics and questions, and stuck to the 30-minute time commitment. The takeaway for me was significant, and in many instances, my mentors were given something in return. People truly enjoy helping other people and sharing their own experiences. The impact this has had on my life is enormous. I now have a network of professionals whom I trust and rely on, and to this day I call many of them friends. It has opened my mind and heart to help others, and allows me to see that we can’t do it alone, and nor should we think we have to.”

—Megan Buzzetta, CEO & President, Global Planners, Inc.

I’d like to hear from you in the comments. What’s one totally unreasonable thing you’re going to consider asking for in the next week as a result of reading this post?

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