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Coaching leaders: how to
get it right… and how to get
it really, really wrong
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
team
leadership
agile coach
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
Ditch the
us vs. them
”It’s you and me vs. the problem, NOT
you vs. me.”
-Steve Maraboli
1.Tips for getting
in the door with
your leadership
team
9
Find a
champion
Understand
leadership’s problems
(from their
perspective)
10
11
Focus on helping them
solve their problems
Learn to
speak
business
Back it up with data
Focus on measurable impact
Structure your communication
16
“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 blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah blah blah blah blah blah blah blah blah
blah
17
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
EnterpriseArchitecture approvals
 Employees report spending 10 hours per week preparing
for steercos & other decision meetings
Key takeaway
Main argument
S1 S2 S3
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
2.Tips for success
once you've
established a
coaching relationship
20
Make coaching plans
TOGETHER
21
Measure impact
(ROI!)
Give specific & actionable feedback
http://www.gsb.stanford.edu/faculty-research/publications/2013-executive-coaching-survey
Go & see
Roll up your
sleeves
(i.e. take an active role in the solution)
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
3.Tips for how to
mess is all up
“agile is a
mindset!”
“be a
servant
leader!”
Arm
yourself
with
platitudes
Keep it
theoretical
29
Point out
all of the
problems
all at once
“Problem talk creates problems,
solution talk creates solutions.”
-Steve de Shazar
Focus entirely
on process
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
• 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
leadership
Coaching leaders: how to
get it right… and how to get
it really, really wrong

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Coaching leaders with Daidree Tofano

  • 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
  • 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. 1.Tips for getting in the door with your leadership team
  • 11. 11 Focus on helping them solve their problems
  • 12.
  • 13.
  • 14.
  • 15. Learn to speak business Back it up with data Focus on measurable impact Structure your communication
  • 16. 16 “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 blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah blah
  • 17. 17 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 EnterpriseArchitecture approvals  Employees report spending 10 hours per week preparing for steercos & other decision meetings Key takeaway Main argument S1 S2 S3
  • 18. 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
  • 19. 2.Tips for success once you've established a coaching relationship
  • 22. Give specific & actionable feedback http://www.gsb.stanford.edu/faculty-research/publications/2013-executive-coaching-survey
  • 24. Roll up your sleeves (i.e. take an active role in the solution)
  • 25. 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
  • 26. 3.Tips for how to mess is all up
  • 27. “agile is a mindset!” “be a servant leader!” Arm yourself with platitudes
  • 29. 29 Point out all of the problems all at once “Problem talk creates problems, solution talk creates solutions.” -Steve de Shazar
  • 31. 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
  • 32. • 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. Coaching leaders: how to get it right… and how to get it really, really wrong

Editor's Notes

  1. A quick note about me, which
  2. Walkthrough & brain stuff Harvard MBA Spun up & sold 3x startups Worked in consultancy for a while Now a director over 80 people Build a little empathy: Never lead at scale
  3. story
  4. 55% deveop next generation of leaders 54% global recession slowing economic growth 52% attracting and retaining top talent 50% driving new product innovation https://www.ddiworld.com/blog/top-ceo-challenges
  5. Make a white version
  6. Make a white version
  7. Make a white version
  8. https://www.blinkist.com/en/nc/new-reader/the-pyramid-principle
  9. Make a white version
  10. If someone comes to you with an issue, it’s not the time to come back with a rehash of the agile manifesto
  11. It overwhelms and frustrates people. Instead, think of what problems exist together, and always offer solutions if you do come with a problem.
  12. One of the first leadership coaching gigs I had, I went in and immediately focused on their process. Process without understanding, context or the mindset shift… so the process ends up not solving issue but creating other issues.
  13. Make a white version