How to sell it to your boss and the L&D department
Summary: You’ve just stumbled across a leadership coaching program that sounds perfect for you. How do you convince your management?
Written by Alistair Gordon 02 Nov 2019

Image credit: Elijah Hall on Unsplash

Imagine this. You’ve just stumbled across a leadership coaching program that sounds perfect for you – it ticks all the boxes and is exactly what you were looking for. Your heart is racing with motivation and your mind is already playing snippets of you walking through the work corridor while all your colleagues stand on either side parting the way for you as they cheer you on.

“It’s because of my wonderful leader that I want to get out of bed and come to work every morning”, you hear one of our team members bragging to the person next to him as he claps you on. “Wow”, the other responds, “I wish I had a leader like that”.

You are about to become the best leader in your organisation.

With all the possibilities running through your mind you snap out of your day dream and run to your boss’ office. You knock on the door with pride, barge in and start rolling out all the facts about the course.

Half way through your boss puts his hand up. You stop and gulp. He looks at you with those judgemental eyes that you have always feared. “A coaching program?” he asks “Too expensive. There’s no way L&D have the budget for it. Sorry kiddo.”

He goes back to his laptop and you turn around, shoulders slumped, and head out the door. ‘I can’t wait to take his job one day’ you think to yourself as you walk away.

Rejection from the boss like this is not uncommon. In fact, the team at HTRYB have experienced it too.

But we soon got clever and crafty about how we ‘pleaded our case’ to the boss and L&D department (and sometimes even the CFO) when there was an upcoming course we wanted to attend.

It’s not your boss’ fault that he or she said no – it’s your fault. You didn’t sell it them in a way that made it sound like a no brainer.

While the tricks of the influencing your boss trade are reserved for the Managing Up and Influencing modules in the coaching program, here are some questions that your boss and L&D are likely to throw your way.

And to help you out, we even provided the answers for you.

  • Why should I develop you, you’re only a Frontline leader.

  • Money, money, money - how much is this going to cost me?

  • Where will I see the payoff? What’s the ROI?

  • Can these skills be transferred?

Ideally after attending the course the person should have a meeting with their team and run through what they have learnt so the company benefits from skill transfer

  • If I send you I’ll have to send everyone else and I don’t have the budget for that.

  • What are the top 3 things you’ll get out of this?

Only 3 things? While we know that you’ll get dozens out of this program here’s a few you might share with your boss:

  • Leadership skills that target my immediate leaderships gaps now

  • The skill to lead others in the way that they want to be lead.

  • A living development plan that will hold me accountable for my own development and that I can share with you in our monthly development meetings

… we couldn’t stop at 3…

  • An understanding of a coaching environment, so that I can replicate the same with my team

  • Building a network within, and sometimes outside of, the organisation. Great for relationship building and networking skills that leaders are increasingly required to possess.

How much work is it, are you going to be able to keep up with the rest of your job? You tell me you’re too busy already.

I most likely have so much on my plate because I don’t know how to manage my time or to utilise my team effectively and are picking up all their left over work. Luckily, the HTRYB coaching program offers modules on time management and setting performance expectations, which means I’ll learn how to priorities my time and delegate the work back out to the team that they should actually be doing. I call this ‘killing two birds with one stone’ – the better I become at leadership, the more I will be able to free up my time for the things I should be doing, like leading my team.

We’ve done this kind of thing before and it hasn’t worked – why is this one any different?

There are a number of reasons why this program is perfect for me and different to any other.

  1. It doesn’t require me to leave the office for days at a time. The commitment is 2 hours (with a bit of travel time to and from the location) once every 4-6 weeks.

  2. The program is tailored to my coaching pod’s immediate leadership needs. The content will resonate with us which means we’ll be keen to absorb what the coach has to offer.

  3. It’s an intimate environment so we’ll more than likely learn from our coaching buddies and really explore our personal leadership challenges. We won’t have a know-it-all taking up all the discussion time from the other side of the room like there usually is in other leadership courses.

  4. I control my development and the responsibility is on me to make a change. I will determine what my development actions are and my coach and coaching pod buddies will help me keep myself accountable.

  5. The content is “news you can use” – no boring lectures or academic speeches. It’s intensive, practical and relatable learning that really sticks. In fact, I can implement what I learn the second I get back into the office.

We have our own programs running in-house so I can’t justify sending you to some external provider.

  • How will learning/improvements be measured?

  • How will learnings be maintained after the coaching program?

  • What support will others in the organisation need to provide?

  • What is the benefit of having an external coach compared to an internal coach/mentor (e.g. manager)?

  • What’s the extent to which the goals of coaching are achievable within the time available, and what are the consequences if coaching does not achieve the intended goals?

  • Do you have time to put workload aside to have regular coaching sessions?

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