Coaching Leadership

Slow is Smooth

We often fall into the urgent trap, thinking that something that’s just come up is the most important thing in the world, and we need to drop everything to pick it up.

That means we end up stacking up lots of suddenly urgent things. Slicing our time between many of them and not actually really making major progress on any. Small amounts of progress on lots of different things is totally worthless.

In contrast, when we are smoothly working through things, we get fast. There are fewer distractions or interruptions, product increments are done and we move on to the next.

We get smooth by going more slowly. Take the time to look at the requests that come in or the issues that are raised. What’s the true impact? Is it really worth dropping everything to pick it up. How much does it cost to stop doing what we were doing, and what’s the cost of delaying the activities we had going on.

Urgent is easy, it’s cheap calories and high fives all round when whatever it is it gets solved.

To balance it, you have to recognise the cost of doing that urgent thing, not just enjoy the sugar rush of jumping on it straight away.

You need to broadcast the costs and impacts of going urgent, managing the expectations of the stakeholder who wants this “Right Now!” and not forgetting the stakeholder who was promised major changes on a longer timeline.

If it’s really urgent and important, then you need to suck up the costs and distractions. If it’s not, then use your usual prioritisation methods to slot this new request in, and keep smoothly delivering valuable outcomes.

If you can stay slow rather than rushing from urgent fire to fire, then you stay smooth and you get more big things done. That’s when real change happens.

Coaching Leadership

What’s the Problem?

There are a wide ranging set of power-move questions that can be asked during a meeting. “What’s the Problem?” is a classic example of the type.

As with all powerful things, it can be used for good, or for ill. If you bring it into play, then try to always be the first and be prepared to defend against the second.

When you use it for good, then you reset a conversation that has dived into detail or solution mode too quickly. It’s really powerful when people are pitching a particular feature or asking for something specific, but they haven’t shown why doing it that way is important.

So you can pull back, understand the problem and confirm if the proposed action is really the best solution to the question on the table. It lets you check the foundations of the argument are sound, and that the work done to get to the solution is solid. If it’s not a sound request, then you are able to a put a pause in place to get to the right final outcome.

The flip side is when someone tries to use this move to derail a fruitful conversation. Maybe they feel like their voice hasn’t been heard and they don’t like the direction that’s been agreed on. Possibly they are only just now paying attention and have missed the discussion up to this point. Sometimes, they just want to feel clever at having made a serious sounding contribution.

To reduce the incidence of the question, lay the groundwork ahead of time. Give out pre-reading as part of the agenda that sets the scene and discusses the problem space. Cover what’s been tried, what’s discarded and what’s on the table now. Next, prep the 90 second summary for the start of the meeting. Outline the problem, share the constraints and set the scene, “This is a meeting to solve this problem”.

Now anyone asking what the problem is can be pointed back to the opening statements, keeping the meeting focused on the solution.

If they disagree it’s the problem to be solved, that’s a different conversation to have. This might be raised early in the session, or they might wait to ask “What’s the real problem here?”. In either case, you can pause quickly and ask what they meant by the question. At attempt to obstruct or bring a new agenda is likely at this point, so ask if there’s any fresh information to consider, and if not, you can thank them for their question, point back to the opening statements and then move on.

If there is fresh information, then it might be an ambush. Something critical to the decision making has been left off the table until the last minute. This is a difficult area to navigate, as whilst the person bringing the info may not be acting collaboratively, the information itself might still be vital.

You’ll need to think carefully about how to handle the conversation, but don’t lose your cool. Thank the person for their contribution, then consider if it’s significant enough to change the parameters of the meeting. If it is, then it’s better to postpone the decision until we’ve included the new info into our parameters. If this happens once it’s something you can handle with private feedback. If it’s a pattern of behaviour, then that’s a time you need to share the impact with the person’s manager, to bring them back to collaborative decision making and proactive information sharing.

Asking “What’s the problem?” can defend you against moving to solutions too quickly, meaning you get to a better final outcome. Use it with care, and understand how to protect yourself from those that ask it with bad intent.

Coaching Leadership

Don’t Burn Your Bridges

As you go on your leadership journey, you will ever more be called upon to use your influence to get things done. You have to convince people, win them round to your way of thinking and show them why what you want to do is important.

That means you have to negotiate. Understand what you want, what you can give and what outcome you are after. You might try to Get to Yes, or you might prefer to Never Split the Difference, but you’ll need to get better at these skills as you’ll need to use them more.

An important thing to realise when you are part of an organisation, is that you’ll be going round the loop multiple times. It’s no good “winning” once if that sours the relationship for the future.

That’s short term thinking, when you need to be in for the long term. You need to think about how to make it better for everyone, so you enhance your reputation as someone great to work with, rather than someone to be avoided at all costs.

Your basic outcomes should always including building the relationship, as you know you’ll be back, whether it’s next week, next quarter or at the start of the next year.

So, don’t burn your bridges, build them up instead and make your future path smoother.

Coaching Leadership

Spend the Money

In the world of tech, it’s really easy to fall for the fallacy that it’ll be cheaper to build it yourself. We’re creative people, we like building stuff, so we can lean towards that approach.

Sometimes it’s the right call, but really often it’s not. Luckily, there’s a few simple questions you can ask to help make the right decision about when it’s right to spend the money.

Is it a key differentiator? – If it’s an important part of the value proposition for you, then it’s much more likely to worth building yourself. If it’s something you just need to do to keep up, then there’s probably something you can just buy.

What’s the true cost of building? – Challenge the assumption that it’ll be easy. Exactly what needs to be done, how many people need to work on it and how long will it take. push back on the “Just a couple of weeks”, and dig in so you are shown the working.

What do you already have? – It might be expensive to put a whole new solution in place, but if you’ve got something that you can extend, that’s often a lot cheaper. Unlocking features in SaaS solutions is often immediate as soon as you choose to spend the money.

Are you willing to compromise? – If you buy something, you can’t full customise it to your every need. You need to accept that you’ll have to work within some limitations, and if you do, then you’ll get the value for what you buy. Bashing into the perfect shape is often more expensive than building fresh, so be really honest here.

So if the problem is:

  1. Not core to your business
  2. Really expensive to actually build out
  3. Solvable by extending existing solutions
  4. Something you can compromise on

Then it’s probably right to spend the money



There are lots of ways to set goals, and lots of ways to get going on achieving them. It’s pretty much the same approach when you are setting your own personal goals as to when you are setting those for your organisation. The difference is in the circle of people you consult with (more professional overlap for the org goals!), and then how widely you share them.

Sharing your personal goals helps you commit to actually making them happen. It’s not vital, but it’s certainly useful. Sharing your org goals is vital! It’s the only way they are going to happen, and it’s the only way that people will know what you are trying to achieve as a group.

Banging them in a slide deck and calling it a day is not going to cut it. That doesn’t give the alignment that you need to have everyone pulling in the same direction to chase down these big goals.

Instead, you need to get your comms plan in gear, figure out the arenas you can sell your goals in. Present them to people, tell them why these particular goals matter and why they are more important than other things we could be doing. Take questions and answer them honestly. Record some sessions for people who are on leave. Share them in Slack, put them on the Intranet (woo!) and finally point people to the deck!

Then repeat this, and go again. Talk about progress towards the goals, share the successful steps towards them and keep them in people’s minds.

This multi-channel approach might get decent visibility and some good buy-in, and the repetition will help, but you won’t actually know how aligned people are to these goals.

Ask them!

As a leader you’ve got more context, you know what’s going on and you have more background than most people in the org. It’s all obvious to you, but it might not be to the Individual Contributors doing the work.

So, ask some questions:

  • What is our top goal for the year?
  • Why are we going after this?
  • What are we not going to do?

Look for patterns in what comes back. What’s missing, what’s wrong, what has actually landed with people? Take these themes, then use them to rework your comms. Address the misconceptions, dive deep into the gaps and celebrate the good understanding.

You build alignment with clear messaging, repetition and rework.

It’s not a one-and-done deck and presentation, and if you think it is you are destined to fail.


Elevator Pitches

You need to be able tell someone what you do, and why it matters, in just a couple of sentences.

We tend to call this an elevator pitch, taken from the idea that you might be in a lift with someone, and you’ve only got the short time it takes to move between a few floors to show them what you can do.

You also need to have more than one of these pitches prepped. Imagine it’s your boss, a peer, someone in a different part of the org or even the CEO. Depending on who you are talking to, you want to be able to show your value in a way they will understand.

First off, get the long list written down. Think about the impact that you’ve had, projects you’ve led or products you’ve launched. List out these wins, cover the business value, why they are interesting to a specialist and what the 50,000 foot view looks like.

Next up, loop round, tighten them up (remember, only 2 sentences!). Take the best couple and practice saying them out loud. You want to loop through enough times that it feels natural to you, that you have the cadence down and that you aren’t rushing-to-fit-in-more-than-two-sentences-in-a-few-seconds.

If you want to go full on “Elevator Pitch”, then you finish off with some sort of hook. You might just want to raise awareness so that you are remembered in future interactions, or you might have some sort of request that you need to make.

In the pitch, you don’t have time for this, so don’t use those seconds to ask for extra people or some more resources. Instead, give the person something that they can come to you with.

Imagine that your value statement is: “We’ve just launched product X to country Y, and it’s driving a Z% uplift in annual revenue.”

That’s super good for your out of org colleagues, and probably works well for the CEO too, as it’s very commercially focused.

Now, if the thing you want is some support to go faster and launch to another country, then assuming that you got a positive reaction, you can follow-up the statement with “Let me book in a meeting to discuss how we can accelerate the rollout”. if you get an enthusiastic yes (or even a “Speak to my PA”), then you are much closer to reaching your goal than if you either went direct, or made the request without the pitch first.

So build your pitches, practice them. Refresh them to keep them current and tailor them to your audience. Raise awareness or leave a hook for future conversations.

A thousand times better than an awkward silence and a chat about the weather!

Coaching Leadership

Make your choice

I recently joined a webinar discussing Effective Engineering Leadership. One of the questions was around remaining current as an Engineer when making the change to a management role.

My advice here is to think about the job that you want to do, and focus on that. You need to make a choice between the Individual Contributor role and the People Management role, as they are different jobs with different skillsets.

You can trial one or the other for a period of time, but if you try to do this for a long time, you’ll just end up doing two jobs badly, which is not a great outcome.

On either path you can still be a leader, and in fact that’s expected as you progress and grow your career. Good organisations will support this and have development paths for both tracks. Bad ones will force their best ICs to management. Choose where you want to focus your efforts!

Nothing is also a choice, but in your career doing nothing and just drifting along is likely not a good one.

So pick a role, understand it, learn the skills you need to be successful and deploy them. Don’t do two things badly.

Coaching Leadership

Everything Old is New Again

In a large enough organisation, it is easy to lose the thread of where we are now. Great practices and processes can be lost as people move on to different roles or focus on new things. As you grow, people joining the company will bring their own experiences forwards, without necessarily understanding the history of what has gone before.

This is another classic communication conundrum, having people tread the same ground multiple times, solve problems that have already been solved or go chasing off in multiple different directions is incredibly wasteful. What can you do to reduce the likelihood of this happening?

Document the good stuff! People are unreliable over time, so write it down if it’s good. Give access to people who are interested in the specific topic, and make sure it’s easy to edit and keep up to date. This is great for repeatable processes like hiring, and it’s super good for recording decisions, especially when you choose not to do something.

Next, make sure there’s someone who has responsibility for the thing, and time to manage it. For small stuff, that might be part of a role, but again, as you grow you might find it’s important enough to hire someone, or build entire teams around it. I’ve taken onboarding practices from an ad-hoc group of volunteers, to a defined part of people’s roles, to the entire job of a small team. This gives amazing continuity and saved us from re-inventing the wheel multiple times.

Then you need to communicate it. Remind people where things are stored. Ask them if they have seen the docs, or talked to the people who are already doing the thing. Connect them up. If someone is keen to improve a recruitment practice, hook them into the groups already working in that space.

If people are new and want to investigate a product area that’s previously been discounted, then accelerate them by giving them the state of the art. Get them to answer the question “What’s changed?”, and they’ll save massive effort on getting to where you have already been, and be well prepared for any long-serving nay-sayers they meet on the path.

Also, make sure the people who are already doing a thing are easy to find and noisy about what they do. This is when you broadcast, that’s where you share your wins on the public channels. That’s an excellent use of the wiki, intranet or company Slack. Help people find you early, and you don’t crush their dreams when you tell them that you’ve already solved that problem.

It’s poisonous to leave people solving problems you’ve already solved, it’s the quickest way to waste massive sums of money and great tracts of time. Build that organisational memory, and propel people to the novel and new.

Innovate in fresh areas to drive on to great success.



We are terrible at quantifying and understanding risk. More often than not, we err on the side of positive outcomes, especially if we think something is pretty likely to happen. You can explore this deeply in the classic Thinking, Fast and Slow, but today we’ll look at risk vs optimism in software development planning.

If something is complex, novel or collaborative, then it’s really hard to plan, with software, it’s all three! Previously we’ve looked at the reasons why we use agile methods, and why launching early is important to the creative endeavour, and why “When” is a bad question. Now we’ll bring some number to the party. Exciting!

Sometimes we need to hit a particular date or milestone, usually when there’s an external requirement (think a new law coming in to force, or an immovable date like Christmas). How can we understand the risk we are facing, and also report them out accurately?

Optimism is not our friend in these circumstances. There are a number of ways to be optimistic when planning against these fixed dates, here are the top three:

  1. This is an easy problem to solve
  2. We’ll get faster as we go
  3. Nothing unexpected will happen

A new or na├»ve planner will come up against all of these, but might not recognise them. They will look at the requirements, split them up, estimate them and slot them into your preferred timeboxes. Almost certainly this means your plan will slip and you’ll miss your target.

Imagine that you hit sprint commitments 90% of the time. That’s pretty good! However, that means within five sprints, you have more than 40% chance of missing a commitment. As soon as you miss one, you are playing catch-up, and experience shows us that never actually happens.

Being right 90% of the time is also massively unlikely, but it’s a nice round number that’s pretty comforting in planning world. If you only really are spot on 75% of the time, then after 5 sprints you’ll have missed at least once move than 76% of the time!

To beat this optimism, put some evidence into your thinking. Track two things. First off, how hard you thought something would be at the start. Second, the end-to-end time to complete it (which includes everything to get it really and truly done and out into the world).

Generally, we’ll perform about as well as we did last time. Maybe a little better, possibly a bit worse, but tracking these two numbers mean you’ll be able to get good confidence in how often you hit those commitments.

Next up, grab some contingency. If you have a fixed date, then aiming at that time is the high risk approach. Remember, you are super likely to slip up, even if you are right 90% of the time.

Assuming that 90% figure, if you extend that five sprint timeline to six, then the chance that you miss commitments twice is only 18%. That’s over 80% confidence of success, much better than your 60% working to 5 sprints exactly.

These calculations can be performed with the help of a binomial distribution. It’s all pretty theoretical, but it can help to shed some light on unexpected outcomes.

Finally, do the things that are most important first. That’s a key part of success in the agile world, and it still helps even with the fixed commitment.

It’s not always the hardest things, but the ones that matter most. If there’s a feature you simply must have or else risk breaking the law, then do that first. If it’s nice to have, or a general solution to the problem, or something else that’s not vital, put it to the back of the queue.

This means that even if you do end up missing more than expected, at least you’ve done the biggest bits first. When a deadline is looming and you’ve got the ‘Musts’ done, then the ‘Maybe’ quite often just falls by the wayside.

These techniques help you overcome optimism, plan better, be more agile and keep more of the commitments you make.

Measure the difference between your estimates and the actual time taken, grab contingency and do the important things first!

Coaching Leadership


Effective delegation is a vital skill to scale your efforts as a leader.

As with any skill, it takes practice to get right, and it’s certainly something you can get wrong. Bad delegation is an abrogation of responsibility, it leaves people confused and uncertain, and it’s a super quick way to confirm any rumours that management is ‘out of touch’.

Good delegation is a powerful way to develop people in your organisation, and to get them ready to take on aspects of your role, so you can step up to the next level yourself.

Look out for opportunities that align to the development needs of the person you wish to delegate to. That could be their strengths to take to the next level, or it could be a gap where they need to show stronger competencies on a wider stage.

Early on, it can be hard to let go. Use the 70% rule. If you think the person is going to be at least 70% as effective as you, then they are ready to take on the delegation. Don’t wait until they are 100% ready, especially if you lean towards perfectionism. This is because your judgement is going to be somewhat off, if you think 70%, it’s more likely they are just about there, and if you think they are 100%, then it’s likely they were really ready a long time ago.

Also, start small. Don’t delegate a year long project, start with something that runs for a few weeks at most. It’ll be easier to track progress, and failure here is likely to be less than catastrophic.

To ensure a good delegation experience, you need to set solid expectations, you need to show trust and you need to verify what’s going on. It’ll be rocky the first few times, so check-in on these as you go, and don’t be afraid to reflect and correct.

  • Expectation – This sets clear boundaries, you explain what the goals are, what the parameter are and especially what success and failure looks like.
  • Trust – You then need to give space to the person to achieve the outcome. They won’t do it like you would, so don’t micromanage
  • Verify – Trust the process, check-in on the progress. Agree when you’ll do this as part of the expectation setting, and scale it based on the importance and duration of the task. Daily check-ins on a yearlong project are probably too often, but might not be for a week long effort. Make sure it’s close enough together to enable easy course correction, but far enough apart to avoid constraining creativity.

Use these techniques, and you are much more likely to turn delegation into a great development opportunity rather than an abrogation of responsibility.