Scaleup Leaders: Stories from Experience

Ben Legg is the co-founder of The Portfolio Collective, a company that helps people build portfolio careers and helps companies hire fractional talent. He works with startups, investors and thought leadership.

In our interview he talks to me about side hustles – something he’s been doing since his teens – building your portfolio of careers and eventually ditching the day job.

Find out when you should be thinking about starting a side, why it’s a good idea in this time of job uncertainty, and how to go about it in the most optimal way.

In this episode I go through my 5-step process for the execution of OKRs.

You've got your OKRs set up, and now it's time to do the work and actually execute them.

In this episode I cover:

Planning - A basis for change

Reviewing - Iterate and socialise

Weekly Meeting - Create momentum and course correct

Weekly Review - Capture problems and wins

Weekly Recognition - celebrate the wins!

The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead.

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

These are questions I collected over the last weeks from comments and questions asked by future and current clients.

0:04:20 - My CEO is incompetent. What should I do?

0:10:10 - How can I use OKRs to measure productivity objectively?

0:15:13 - My product and engineering team isn't trusted by the rest of the organisation. How do I create trust?

0:28:33 - Can OKRs work in a hybrid, remote or in-person environment?

0:32:12 - In a multi-level organisation, it takes too long to set OKRs at each level and align them with each layer above. What should we do?

The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead.

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

I had the pleasure of being interviewed by Allan Boyle of Saltwater Consulting. Allan helps Technology companies Scale Well, and we are both Amazon alumni, so it was good to catch up with him and discuss OKRs in the Scaleup context.   

Find Allan on LinkedIn here: https://www.linkedin.com/in/allanboyle-transformation/

Allan's website: http://saltwaterconsulting.ie/

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The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead. 

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

I was asked by a client (a large multinational) to hold a Q&A on OKRs. They have a large team of OKR coaches and wanted my perspective on several issues they were dealing with. 

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The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead. 

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

Amanda Colpoys knows how to 👉 remain nimble at scale. 👈

She has helped grow Moonpig, Gousto and OVO to unicorn status.

Here’s what we discussed:
👉 What lack of strategy does to your focus
👉 How to create and maintain alignment (OKRs may help!)
👉 Coaching to enable autonomy and empowerment

Connect with her on LinkedIn here 

https://www.linkedin.com/in/amandacolpoys/

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The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead. 

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

What are the root causes for people problems in Scaleups?



I will be talking all things Team & People



with my friend and former colleague Janie Links.





Janie started her career 20 years ago as a headhunter.



And her roster of clients and employers reads like a Who is Who of London tech:



Google, Criteo, Wonga, The Trainline.



She has seen it all in Scaleups - the booms, the busts, the hiring frenzies and the layoffs.



Now, Janie is running High Calibre People, a HR consultancy, where she advises Scaleups on all things people and growth.





Time Stamps:

00:02 Welcome & Intro

03:33 Janie’s clientele

05:43 Janie’s entry process

09:16 When do clients need Janie

11:30 Diagnosing the gaps in your business/team

14:30 Janie’s level of involvement in teams' development

16:10 How your people strategies support company/clients goals

21:05 On having great leadership

26:20 When to do leveling

32:20 On calibrating people & expectations

36:19 How OKRs relate to leveling

42:09 Equity vs. Cash

46:10 Advice for companies setting up a talent engine

49:50 Hiring at the right level & justifying them

53:50 Janie's top tips

56:40 Wrapup

Learn more about Janie here: https://highcalibrepeople.com/

and here: https://www.linkedin.com/in/janielinks/

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The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead. 

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

Dora Nagy has worked at Google in Product Marketing and Global Sales Strategy and Operations, and at SoftBank and Kheiron Medical as Chief of Staff. She's an accomplished executive coach for high-growth startups.



Dora and I discuss what a Chief of Staff is, why your company needs (or doesn't need!) one, and what makes a great Chief of Staff.



We also dove into some of her experiences working with founders and exec teams as a CoS or coach, her experiences with OKRs and other systems, and much more.

Time Stamps:

00:04 Welcome & intro

01:39 What is a Chief of Staff?

05:42 The between a COO & Chief of Staff

08:01 The Chief of Staff framework (the 5 Ps)

11:09 Why and when do companies need a Chief of Staff?

13:19 The evolution of a Chief of Staff

15:40 Layers of a Chief of Staff

18:40 The relationship between the Principal & Chief of Staff

20:08 Things that could go wrong between a Principal & Chief of Staff

22:05 Chief of Staff vs Executive Assistant

24:31 How should someone external work with a Chief of Staff?

27:03 When should founders approach Dora?

28:34 Dora's experience with the 5 Ps

35:02 Dora's thoughts on disagreements within the team

39:52 How Dora finds consensus in different types of companies

42:56 Dora's coaching experience

45:10 The importance of strategy & vision

48:57 The power of cross-function conversations

50:42 Tool to make it work

53:27 How & where to reach Dora

55:50 Wrapup

Learn more about Dora from her website:

www.doranagy.com

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The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead. 

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

It's time for a Q&A. 

These are question I collected over the last weeks from comments and questions asked by future and current clients. 

0:01:47 Our output metrics take more than a quarter to see a change - how do we set OKRs for such a short period?

0:07:31 What's different about OKRs in scaleups vs. more mature companies?

0:10:38 If we use OKRs to say no to other work, how do the urgent and important things that come up during the quarter get done?

0:18:36 Can I use OKRs to transition from a sales-led organisation to a product or customer-led organisation?

0:22:39 Can I use OKRs in my personal life or in my relationships?

0:27:46 We use SAFe, the Scaled Agile Framework, so we already have a cadence. How do we integrate OKRs with that?

0:36:04 How do I convince my management to adopt OKRs?

0:44:18 How do I get executive buy in for my OKRs?

__________

The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead. 

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe

So you’re half-way through the quarter



Should you check in on the progress of your OKRs?



That’s what we cover in this episode:

✅ How to check if you're on track

✅ What to do if you aren’t

✅ How to run a meeting usefully

✅ How to manage expectations up and across

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The Scaleup Leader is a podcast about helping fast-growing tech companies scale better and execute faster with OKRs

I (Richard Russell) am an ex-Amazon & ex-Google product tech lead.

Connect with me on LinkedIn www.linkedin.com/in/richardarussell

And subscribe to my twice monthly email on www.richardrussell.co/subscribe