Leveraging Coaching Skills as a Leader: Making a Request

kara • May 31, 2022

Amsterdam is famous for its bicycles. In many ways, the city was designed for cyclists; the laws almost always favor cyclists! And so it is no surprise that when Stephanie and the rest of her family went to visit her sister who was living in Amsterdam, they found themselves following behind her sister and riding a pack of bicycles.


Stephanie’s sister played tour guide for the entire family during the visit… but she wasn’t everyone’s favorite guide. When the group went on an outing, the bicycles would span the length of a city block or two! They’d bike along in a long clump, the light would turn yellow, and then rather than slowing down and waiting for the family, her sister would speed up to make the light, only to leave the rest of the family stuck behind a red light without any idea where they were heading next.


Stephanie’s sister had been living in The Netherlands for several years at that point, and had managed to merge her New York City assertiveness with the strong pro-cyclist attitude encouraged in Amsterdam. The result? A rather aggressive, confident biker who knew just how long the light would stay yellow and just how quickly pedestrians would get out of the way when she rang her little bell.


This happened enough times that finally a family member complained. “Can you ride slower?! Don’t you realize that we are a whole block behind you and can’t catch that yellow light if it’s already yellow for you?!”


The peanut gallery had a lot of comments…”You’re always so aggressive.” “Can’t you be more considerate?” “She’s just like that. Always has been, always will be.”


They were stewing in it. And Stephanie’s sister who was so excited to be the local host felt attacked.


And then Stephanie had an idea. She was in the process of pursuing her coaching credentials, and in her coursework had read about the skill of Making a Request. The concept is that a request can challenge a person to take their game up a level while not shaming or bullying them into doing something they are not ready to do. She decided to try it out. The conversation went something like this:


Stephanie: Hey sister, what was important to you about taking us all on a tour of the city?


Sister: I wanted you all to see the sites that I love, and experience the joy of riding around in a city designed for bicycles.


Stephanie: Ok great! How do you think we’re doing?


Sister: We’ve seen a few of my favorite places. Why?


Stephanie: I agree we’re getting through the sites. How about your other goal… experiencing the joy of riding around in a city designed for bicycles?

Sister: I dunno. You guys are all super slow and annoying.


Stephanie: In this instance, are you more focused on experiencing joy yourself, or having us experience joy?


Sister: I guess I want to focus on the experience for you guys.


Stephanie: Fair enough. Can I make a request?


Sister: Fine. What?

Stephanie: Right now my experience is more characterized by stress and less joy than I think you’d like. What would help me is if I felt like I wasn’t going to lose you as my tour guide at any moment. For the afternoon, I have a request for you: When at an intersection, will you look behind you and consider how long our trail is before you decide to cross? You can accept, reject, or negotiate my request.


Sister: Ok. I can do that.


That request instantly changed the dynamic.


Stephanie’s father even clapped his hands and let out a whoop celebrating a new kind of sisterly interaction he’d never before observed. The crew went back onto the streets, Stephanie’s sister still out front, but now as a more attentive custodian to the goal of the day.


When they returned to their hotel, the whole family commented on how pleasant the afternoon riding was.


We share that story because there’s a lesson there for manager-employee interactions. Some of our clients are new to managerial roles, or they’re stuck with a difficult employee who doesn’t seem to “get it.” Our clients tell their employees what they expect. They show them what to do and how to do it. They repeat themselves over and over, and then throw their hands up in exasperation. 


A request is defined by the Merriam-Webster dictionary as ‘the act or an instance of asking for something’. From a coaching perspective, this definition falls short. A request, in our opinion, is made when we see untapped potential or an opportunity not being fully leveraged within a person. At its core, a request is a gift of possibility available to the person who chooses to receive, unwrap and appreciate the request you have made.


As a leader, this approach to making a request can be transformative. Rather than directing (“I need you to complete the report by this Friday”) or reframing that directive as a question, (“Can you have that report done by Friday?”), a great request comes from a place of seeing true potential and opportunity (“I have a request for you. Will you get that report to me by Friday? You can accept, decline, or negotiate.”)


What’s crucial to notice about a well-formulated request, is that it first challenges the person to do something big, but then is followed up by explicit permission to counter-offer or flat-out reject the proposal. This is important because in manager/employee relationships, there is always a power dynamic at play. By offering your employee permission to say something other than “yes” you empower them to step up and articulate what they WILL do while simultaneously holding them up to what you know they’re capable of.



The next time you ask an employee to do something, try shaping it as a powerful request. What do you notice happens as a result?

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