The document provides tips for coaching leaders effectively and ineffectively. For effective coaching, it recommends finding a champion, understanding problems from the leader's perspective, focusing on problem solving, learning business speak, making plans together, measuring impact, and giving actionable feedback. For ineffective coaching, it suggests relying on platitudes, keeping things theoretical, only pointing out problems, and focusing solely on processes.

1. Coaching leaders: how
to get it right… and how
to get it really, really
wrong

2. 2
For the past 4 years, I’ve has been working
with leaders and executive teams to:
• Navigate the mindset shifts needed to
be effective in complex environments
• Role model new behaviours
• Hone their own unique leadership style
• Create effective, well-aligned exec
teams
Now I am a director, so I get to practice
what I’ve been preaching (it’s hard!)
Daidree in a nutshell
Software developer -> enterprise agile coach

3. team

4. leadership

5. agile coach

6. 1. Tips for
getting in the
door with your
leadership team
3. Tips for how
to mess it all up
(with harrowing
personal tales)
2. Tips for
success once
you've
established a
coaching
relationship

7. Ditch the
us vs. them
”It’s you and me vs. the problem,
NOT you vs. me.”
-Steve Maraboli

8. A quick note
on imposter
syndrome

9. 1. Tips for
getting in the
door with your
leadership team

10. 10
Find a
champion

11. Understand
leadership’s
problems
(from their
perspective)
11

12. 12
Focus on helping them
solve their problems

13. Learn to
speak
business

16. Learn to
speak
business
Back it up with data
Focus on measurable
impact
Structure your
communication

17. 17
“We have a bit of a problem in the teams.
As you know the teams are busy working
on [x product], and have been experiencing
a lot of issues with cycle times in delivering
their work. They’re also just not very
happy. What are they not happy about?
Well, they feel pretty demoralized about
not being able to make decisions, and they
spend a lot of time waiting for other
people to make decisions. I think it would
be great if you interact with the teams like
more of a servant leader, and delegate
authority to them.”
Blah blah blah blah blah blah blah blah
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18. 18
Clarifying and devolving decision-
making authority about product releases
will enable us to deliver value sooner
1. Current decision-making processes cause time delays
§ Work is blocked 30% of the time awaiting decisions
that happen outside of the team
§ Every feature we deliver spends 20 days pending
Enterprise Architecture approvals
§ Employees report spending 10 hours per week
preparing for steercos & other decision meetings
Key takeaway
Main argument
S1 S2 S3

19. Tips for getting in the door
with your leadership team:
• Find a champion
• Understand leadership’s
problems
• Focus on helping them
solve their problems
• Learn to speak business
Recap

20. 2. Tips for success
once you've
established a
coaching
relationship

21. 21
Make coaching
plans TOGETHER

22. 22
Measure impact
(ROI!)

23. Give specific & actionable feedback
http://www.gsb.stanford.edu/faculty-research/publications/2013-executive-coaching-survey

24. Go & see

25. Roll up
your
sleeves
(i.e. take an active role in the solution)

26. Tips for success once you've
established a coaching relationship:
• Make coaching plans together
• Measure impact
• Give specific & actionable
feedback
• Go & see
• Roll up your sleeves
Recap

27. 3. Tips for how
to mess is all up

28. “agile is a
mindset!”
“be a
servant
leader!”
Arm
yourself
with
platitudes

29. Keep it
theoretical

30. 30
Point out
all of the
problems
all at once
“Problem talk creates problems,
solution talk creates solutions.”
-Steve de Shazar

31. Focus entirely
on process

32. Tips for how to mess is all up:
• Arm yourself with
platitudes
• Keep it theoretical
• Point out all of the
problems all at once
• Focus entirely on process
Recap

33. • Find a champion
• Understand
leadership’s
problems
• Focus on helping
them solve their
problems
• Learn to speak
business
• Make coaching
plans together
• Measure impact
• Give specific &
actionable
feedback
• Go & see
• Roll up your
sleeves
• Arm yourself with
platitudes
• Keep it theoretical
• Point out all of the
problems all at
once
• Focus entirely on
process

34. leadership

35. Coaching leaders: how
to get it right… and how
to get it really, really
wrong