10 Lessons Learned in Training Knowledge Workers

by | Mon 1 Aug 2016

Earlier this week, @naval (CEO and co-founder of AngelList) asked a question on Twitter:

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At the heart of his question is an interesting observation. As automation and artificial intelligence replaces manual jobs, how do we retrain people in the new knowledge economy where information handling and management is in high demand?

I thought I would share some experiences, observations, and recommendations based upon when I did this previously in my career.


Back in 2004 I was peddling my wares as a journalist, writing for the tech press. I was living in the West Midlands in England and heard about a new organization in nearby Birmingham called OpenAdvantage.

The premise was neat: open source was becoming a powerful force in technology and OpenAdvantage was set up to provide free consultancy for companies wanting to harness open source, as well as individuals who wanted to upskill in these new technologies. At the time in the West Midlands lots of industry was being automated and moved out to Asia, so lots of Midlanders were out of jobs and looking to retrain. This required, by definition, retaining the workforce as knowledge workers.


OpenAdvantage was funded by the UK government and the University of Central England, had a decent war chest, and was founded by Scott Thompon and Paul Cooper (the latter of which I met when he heckled me at a talk I gave at a Linux User Group once. 馃檪 )

So, I went along to their launch event and wrote a piece about them. Shortly after, Paul and Scott invited me back over to the office and offered me a job there as an open source consultant.

I took the role, and this is where I cut my teeth on a lot of open source, community, and working with businesses. We had crazy targets to hit each month, so we ended up working with and training hundreds of organizations and individuals across a wide range of areas, and covering a wide berth of open source technology and approaches.

All of our services were entirely free IF the person or organization was based in the West Midlands (as this is the area our funding was supporting.)

Training Knowledge Workers

So, what lessons did we learn from this work that can be applied to Naval’s question? I have 10 primary recommendations for training new knowledge workers…

1. Understand your audience and their diversity

Many people who are being retrained will come from varying backgrounds and have different levels of experience, goals, insecurities, and ambitions. As an example, some people may not possess the foundational computing skills required for the topic you are training, yet others will. Also, there may be different concerns about connectivity, social media, and networking based on how much your audience have been exposed to technology.

Be sure to understand your audience and craft your training to their comprehensive set of needs. A good way to do this is to survey your audience before they join. Then you can tune your training effectively.

2. Teach skills that have clear market value

When someone needs to change careers, their top concern is usually supporting their family and bringing financial security to the home. They will only consider skills that have clear market value. So, be aware of what the market needs and train based on those skills. The market is ever changing, and thus are the requirements, so adapt your program to these needs.

So, even though you may love Haskell, if the market is demanding Ruby developers, teach Ruby. Sure, you may love SugarCRM, but if the market demands Salesforce, do the same. One caveat here though is always keeping an eye on new trends so you can provide training on technologies and services as they ripen so you can equip your audience for the very best and most timely opportunities.

3. Tie the training to direct market benefits

Aside from market value, you also want to ensure your audience understands the potential of acquiring those skills before they embark on the training. Benefits such as job security, good salaries, health/insurance benefits, and more can be a useful forcing function that will get them through the training.

Also be sure to train a mixture of vocational skills (e.g. technologies) as well as best practice, methodologies, and approaches for being successful in the workplace. This could include topics such as project management, leadership skills, time management, and more.

4. Provide training at zero (or very low) cost

One of the major benefits of our work at OpenAdvantage was that we provided free services. This made it a no-brainer for many people to consume these services.

You should also try to engineer a situation where your training is also a no-brainer and the cost is free or as close to free as possible. If you charge a high sticker value for the training, many people may not be able to justify or afford it.

A good way to offset costs is with partnerships and sponsorships. Explore different vendors to see if they can sponsor the training, talk to local chambers and charities to see if they can help, and see if local businesses can provide venues, equipment, and other resources to keep the costs low and your training as accessible as possible to your audience.

5. Build in clear intrinsic/extrinsic rewards

For the training to really succeed, the audience needs to gain both intrinsic rewards (such as better capabilities, confidence, digital literacy etc) and extrinsic rewards (material items such as t-shirts, trophies, mugs etc).

Focus on the intrinsic rewards first: they are the confidence and opportunity boosting benefits that will get them over the hump to changing careers and succeeding in their new profession.

The extrinsic rewards can be a boon here though, but where possible, ensure they are useful in their career development. Items such as notepads/pens, USB sticks, books, training materials, and other items are good examples that can support your audience and make them feel rewarded. Avoid gimmicks or tat that doesn’t play a functional benefit as a knowledge worker.

6. Teach by doing, not just by presenting

Having someone sit down in front of a day of presentations is boring. Instead, present short bursts of core skills, but get your audience doing stuff, talking, and working together. Have them execute tasks, experiment, and play. This is what seals the skills in.

My favorite approach here is to teach multiple short presentations (15 minutes or less) and then provide a “challenge” or “task” for them to complete to exercise these new skills, explore, and experiment.

This is important not just for skills development but it also encourages your audience to talk to each other in the session, collaborate, solving problems together, and build relationships.

7. Provide follow up service and connections

It is tempting to assume that when that exhausting day of training is over, you are done. Not at all.

Always follow up with your audience to see how they are doing, introduce them to local communities, show them useful tools, introduce them to other people they may find helpful, connect them to organizations looking for staff and more.

Retraining people is not just about soaking up knowledge it is about bridging the gap to new industries and the people within them. These additional recommendations, connections, and introductions can often be one of the most empowering parts of the overall experience.

8. Teach them how to teach themselves

One of the major challenges with education is that it often teaches skills in a vacuum. Sadly, this just isn’t how the world works.

The most capable and successful people in the world develop the abilities to (a) always learn and grow new skills, (b) always be willing to challenge themselves and their assumptions, and (c) be willing to experiment and try new things. This is a lifelong process, but you should help your audience to learn how to teach themselves and expand their skills.

For example, teach them how to research problems online, how to find support forums and groups, ask meaningful questions, and how to experiment, debug issues, and solve problems. These are critical skills for knowledge workers to be successful.

9. Teach streetsmarts

Another element that is often sadly lacking in traditional education are streetsmarts such as modern trends, memes, and methods of engaging in technology and beyond.

Teach your audience some of these streetsmarts. Examples of this could include the do’s and dont’s of online communication, how to deal with trolls/critics, trending technologies and cultures, how to be successful in an internationally diverse world, and other areas. Again, this will reinforce their capabilities beyond the skills they need to do a job.

10. Build their confidence

One of the most notable things I remembered from my OpenAdvantage days (and have seen since then) is that a lot of people who are transitioning into the knowledge economy feel overwhelmed by the task. They often feel there are too many tools, too many things to learn, that they will never figure it out, and sometimes that they are too old to get started.

This is insecurity, and it can be conquered. The vast majority of people can traverse the challenge and do well, but they need confidence in themselves to get over the bumps in the road and that feeling of being overwhelmed.

Give them that confidence. Help them to understand that this is just technology, and it often looks harder than it really is. Help them to see their potential, what benefits this will open up for them, and how much bigger the market opportunity will be for them. Remind them of the abundance of choices that will open up to them, the confidence it will give them, and how their social and professional networks will grow. Remind them of the good they are doing for their family and the brighter future they will be building.

So, there we have it. I hope some of these learnings are useful to those of you doing this work, and I hope this provided some food for thought for Naval’s question on Twitter.

I would love to hear your thoughts too. What other ideas and methods can we use to make it easier to retrain people as knowledge workers? Which of my points can be expanded or improved? What are your stories from the trenches? Let us know in the squarkbox…

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