If Only I Had Asked ... Making Skillful Requests

Next in our series of essays on the Relationship Course Correction Menu is making a request.  On a daily basis, all around the world, people are making millions if not billions of requests a day, and they are being fulfilled.  Some of these are explicit requests like “Could you make some copies of this for me?” or “Could I have a hug?”.  Some of them are more implicit, like when someone tells you that the pants they are wearing are new, but what they’re really saying is “Could you please compliment me on them?”  It is wise to spend some time contemplating all of those normal natural requests that are fulfilled without much ado.

Some changes are life changing. This is one of the bigger ones.

In this essay, though, we’ll be discussing those requests that are a little more dicey.  Maybe it’s a bigger or more unexpected thing that you’re asking for, or maybe the possibility of rejection seems overwhelming.  For whatever reason, some requests are just more difficult.  For these more difficult requests, it’s good for us to make some preparations.  We need to do what we can to prepare our mindset, and we need to know how to ask skillfully, in order to give us the best chance of having our requests fulfilled and to respond resiliently if they are not.  Here are a few tips:

Ask Clearly and Directly

Once upon a time, I hinted to my supervisor that I wanted to go to a particular conference.  In my mind the hint was quite clear, but I was talking to someone who was particularly deaf to hints, and who appreciated a much more direct communication style.  When the registration window had come and gone, it came out that she had no idea that I was asking to go to the conference.  She recommended I ask more directly for what I wanted.  I had the feeling that I had shorted myself by putting my request into an unreadable code instead of asking more directly.

The next year I asked clearly and directly if she would approve the budget and time for me to attend the conference.  To be honest, she still said no, and she was kind of mean about it. Nevertheless, I felt more pride and satisfaction in the outcome than the year before, because I had learned to be more direct and assertive in my communication.

Ask for 100% of What You Want

Sometimes we end up doing both sides of a negotiation, watering down our requests in the hope of making them more palatable to the person we’re asking.  While there may be exceptional circumstances where this could be effective, in general I advise against it.  If you can summon the courage, begin by asking for 100% of what you want.  Later in the negotiation, if a counteroffer that is lower still has value to you, you can accept a compromise at that point.  

Understand their Path to Progress

I once provided some job coaching to someone who wanted her boss to approve the budget for her to attend a conference.  As she was speaking about it, she emphasized the benefits that she wanted to get out of it, namely to expand her knowledge and her professional network.  I advised her to think more about the benefits to her boss and her other teammates related to the conference.  Would she be able to learn best practices that would improve the work of the department?  How would she share the knowledge that she gained when she got back to the office?  By rephrasing her request as an investment that could help the department achieve its goals, her boss was able to see the value that was in it for her to approve the request.

Before you make your ask, put yourself in the other person’s shoes.  What do you know about their goals in life, particularly as they relate to your relationship with them?  In the workplace the motivation of a staff member who just wants a stable income that allows them to retire is much different from the motivation of someone who is driven to make their mark by getting promotions.  Is there any way in which fulfilling your request can also be seen as a path to progress in their life?  If you’re not clear on someone’s path to progress, you might want to pave the way for your request by practicing listening.  Once you have a better sense of their path to progress, you’ll hopefully be able to phrase your request in a way that makes the benefits to them more clearly.

Prepare to Be Disappointed

Adult behavioral change is difficult.  By the time we are grown ups, we have developed a repertoire of behaviors that are second nature to us.  Some of them may generally be adaptive and lead to good results, others maladaptive and causing problems for us.  Even when we ourselves are motivated to change our behaviors, for instance around diet or exercise, we often fail.  The odds are even worse when we are trying to change our behavior based on a request from someone else.  We must be prepared to hear “no” when we make requests like this.  The best thing we can do is to make a simple promise to ourselves, that we will tend to our own hurt feelings if we are rejected.  If you’re bent out of shape because a request of yours was rejected, it might be time to practice serenity.  

Learning to remain optimistic even after hearing “no” can create a lot of benefits in our lives.  Salespeople who are natural optimists have unrealistic expectations of how many people will say yes to their offers.  Despite this lack of realism, they still make more sales than people who are more realistic.  The reason why is simple: they ask more people.  If we don’t make requests because of fear of rejection (even if that is “realistic”), we leave a lot of value on the table, both for ourselves and for others.  On the other hand, if we learn how to bear the disappointment of hearing “no”, we’ll hear “yes” a lot more than we would otherwise.  

The Dangers of an Empty Yes

My wife recently made a request of me to routinely go into our budgeting program and categorize different transactions.  I agreed readily, and I fully intended to do it.  But then I didn’t.  Not my proudest hour, but I’m out here being honest with you all. 

This is a very common issue with requests.  At the time that someone says “yes” to your request, they get to live in the pipe dream that it’s going to be easy for them to make this change.  They may even feel proud of their resolution for change, before they even lift a finger to change.  I sure did.

As the one making the request, you need to be vigilant that the person is actually as good as their word.  If they’ve made an explicit agreement with you and they’re not keeping it, you’ll need to try more drastic measures, such as providing constructive feedback or describing a fork in the road.  These interventions will be covered in future essays in this series, so stay tuned!

When You See Changes

If your request is honored by the other person, not just in words but in action, make sure that you offer them positive feedback, even if initially the changes you see are incomplete and modest.  Look back at my essay on positive feedback for tips on how to get into the right mindset for expressing appreciation, and how to do so skillfully.

Conclusion

Making requests, particularly higher stakes ones, can be daunting.  You may want to have a coach in your corner to help you prepare, and to debrief the consequences so that you can learn as much as possible from your intervention.  If that’s the case, I encourage you to schedule a free consultation!  

The most important thing is that we live a life with no regrets, which means asking directly for 100% of what we want, phrasing our requests in a way that fits in with their path to progress, being vigilant if the yes we hear turns out to be empty, and showing appreciation when we see changes.  Otherwise we’ll never know how our lives might have been different … if only we had asked.