Brooks: How good are you at making ‘the ask?’

If HR leaders want to drive real change, they must develop one of the most important skills in life: advocating for oneself (and for one’s department!).
By: | March 22, 2021 • 6 min read

Asking for what we need can sometimes seem like a terrifying prospect, but it is perhaps the most important life skill I can possibly think of. I’ve spent the greater part of the last decade deeply immersed in coaching, both as a CEO/executive coach in my private practice and in founding my coaching and mentoring-focused start-up, PILOT. And during that time, I’ve found that, at the core of people finding satisfaction and success, exists the ability to advocate for oneself—and yet, we’re never even really told that we need to do this, let alone trained in how to!

In order for HR leaders to successfully rise to meet the many demands that our organizations have of us, we must first become role models in making “asks” of our colleagues and employers. This is a muscle we also will be well-served in working to develop for ourselves in other parts of our lives—in our relationships, in our families or in our communities. In fact, a decade ago, I experienced a powerful breakthrough in advocating for myself by learning to do so in the context of raising tens of thousands of dollars for a nonprofit of which I was a board member. Once, I had a few cycles in directly asking people for their own money in order to help repeal the military’s so-called “Don’t Ask, Don’t Tell” policy; with them only getting the satisfaction of supporting a good cause and a tax deduction, that experience made asking for budget and headcount at work seem like a breeze.

If asking for what we need is such a central element to leading a life of satisfaction, then why is it that we so often fail to do so? Well, a huge reason is our fear of a “no,” along with the dreaded, self-imposed spiral of shame that can accompany it. In spite of all of our big titles, fancy degrees and years of experience, our egos in the workplace are actually quite fragile, and so we can find ourselves having a tendency to pre-judge what the answer we’d receive would be, if we were to ask. Said differently, we use negative predictions to scare ourselves from even raising the issue, as we haven’t built the necessary resiliency to overcome being let down. However, stop to ask yourself, “When was the last time I was legitimately told ‘no’ to something I asked for?” If it wasn’t recently, then you aren’t advocating for yourself or your HR function enough!

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Back when I first joined the ranks of human resources, pivoting out of management consulting, I knew that I needed to quickly get up to speed on the function, its timeless principles and the latest research, as well as find mentors and the best vendors. To do that, I attended a fair number of conferences in my first year. I’ll never forget sitting around a conference table in our Manhattan headquarters with my peers, most of whom were 20 years my elder, much further along in their careers and making twice what I was being paid, while I was there sharing what I had learned at a recent event. One of them snapped, “Why does Ben get to go to all of these conferences?”, to which our cool-as-glass CHRO gently swiveled her chair in this guy’s direction and quipped, “Because he’s the only one who’s asked to go.” Sometimes it’s that simple!

Occasionally, we can find ourselves dipping our toe into the water by making a half-ask, often over email or a messaging platform, and therefore making it easy for the other party to simply ignore or quickly dismiss our request. It takes a certain degree of courage and conviction to pull ourselves together and directly speak to our needs—be that over a phone line, across a desk or through a Zoom meeting. HR has long been an underappreciated, underfunded and underleveraged function, and I assert that, because of this, we’ve now taken on a bit of imposter syndrome as a profession. Indeed, we’ve trained our organizations in such a way that we will take on more work, more initiatives, more crises and more messes to clean up without ever bargaining for what we need to have in order to actually take on the additional work.

If you’re reading this right now, and you feel that rumbling inside of you saying that it is long past time to ask for what you need to be more satisfied, more successful and more sustainable in your job, here’s how you can do just that.

First, avoid the tendency to make a big deal out of a small ask. Chances are, you’re not asking to buy another company or move the headquarters in the first place, so try and match the level of what a big deal it is to the size of your ask. Then, consider timing, knowing that there’s never really going to be a “best” time to ask, that there are going to be a few “worst” times to ask and that, generally speaking, the best time to ask is going to be soon/now.

When you make your ask, be sure to prepare in advance, so that you can make a concise and clear case—particularly in a way that helps the other person justify giving you what you want, both in their own head and to others, should they be questioned. Tie your ask to the bigger picture of your organization’s goals and strategy—whether it be your direct managers’, the department’s or the organization at large. Set up the stakes, explaining what would change if you got what you needed, and what would be at risk if you didn’t.

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Consider coalition partners, meaning other people who might want or benefit from the same thing, and can either help jointly make the ask or demonstrate that it helps raise multiple boats. Be very specific with exactly what you want, as simply asking for “resources,” “headcount” or “budget” is going to be vague and not actionable.

Remember that the best negotiators are creative, able to remain open-minded to counter-proposals and alternative solutions for getting their ultimate needs met, while remaining level-headed in the process. And like a good salesperson, you should endeavor to be a closer, always defining a next step, timeline, maintaining urgency and pushing for a resolution.

Few things will make you more believable to the C-suite than asking for something in return for a commitment to deliver. And more importantly, regardless of the outcome, the pride you’ll feel in yourself for being the kind of person who asks is a feeling that you’ll find yourself really wanting more of. So, go raise your profile, expand your courage, increase your satisfaction and make that ask!

Ben Brooks is the founder and CEO of the career development platform PILOT. Share your reactions to this column on LinkedIn or @benbrooksny. He writes the monthly Coach's Corner column for HRE.