Want a career full of adventure and tough technical challenges? Excited to see the world? Build a personal brand? Want to grow your ability to create trusting relationships? Consulting may be for you!

I want to reflect on my almost 8 years as a specialized software consultant. I worked in the search relevance space (creating smarter search engines) at OpenSource Connections, which gave me exposure to an invaluable mix of technical and soft skills. Maybe this article will inspire why (and why not) you would want to take on a consulting role.

Why go into consulting? You <3 the deep end!

Consulting initially appealed to me because I enjoyed being thrown in the deep end. My normal work assignments were too easy. In my pre-consulting job, I’d feel bored 2-3 months for every 1 month of really intense challenging work. At the time, in my early 30s, I wanted that intensity all the time.

I had that opportunity and then some! At OpenSource Connections I quickly became the go-to person when the client realized “these search results make no sense!”. I learned to optimize the relevance ranking of search applications, which in the early 2010s, was not something you obsessed about unless you were Amazon or Google. Lucky for me, I was in the right place at the right time to go after this niche and build a personal brand.

However, I soon found that there’s another side to being in this ‘deep end’.

I found myself on the first day of the job apologizing for a former colleague’s shoddy code. I was asked pointedly by the client’s frustrated CTO whether this was typical of our projects and how we could possibly plan to move forward from this point. Another early client was upset with why a question-answering application wasn’t returning the magical results they expected. We had to come with not just a technical plan: but one to clearly communicate concrete expectations on both sides.

These events required me to develop skills I didn’t know I needed - the ability to genuinely build trust and grow my relationship with clients. To see a low point as an opportunity to find a path forward to a better relationship. All in the context to do exciting technical feats to solve their problems.

Shortly after joining OpenSource Connections, my answer to why consulting? became:

1. Nichy - Here’s a really cool niche I can define, explore, learn about!
2. Technical - The technical work is hard and touches on technical areas I care about (intersection of data science and engineering, fuzzy hard to define use cases, intersection of human psychology and technology)
3. Relationships & service - I genuinely valued the hard-won relationships that came out of difficult conversations. These low points were always opportunities to demonstrate I truly cared about a value of service to the client

Consulting: your gateway to entrepreneurship

John Berryman is fond of calling consulting a “gateway to entrepreneurship”. I think this is right, because frankly you act as a mini-entrepreneur as a consultant. You’re a sought-after domain expert that also must develop much needed marketing, sales, and client relationship skills. You care about your niche, and the marketability of your skills all the time.

You learn the only difference between a marketing prospect, a sales lead, and client is only the amount of resources you can devote to them. What does this mean? They all deserve an attitude of service and respect. You build a good relationship and help all of them - person reading your blog, sales inquiry, and paying client - think through tough problems through your work. You are genuine and earnest about serving people, whether they pony up money for your service!

The genuine relationship starts with marketing: before you even talk to them. You demonstrate an attitude towards service in how you engage the market. You write non-spammy, deep, honest blog posts about your field. You give transparent, clear technical talks that barely mentions you provide a service. You do this because you genuinely want to help people. It demonstrates your trustworthiness, which only encourages prospective clients to reach out to you as an advisor in the field.

The relationship continues when you’re contacted by a lead. Sales prospects reach out to you with your first opportunity to assist them. The sales conversation is like the first ‘assignment’ from them by seeking your advice on a tough decision. Almost always the sales prospect is asking themselves some variant of “how do I proceed on this tough challenge at my job for which you are the expert?”.

You must give the sales prospect your best, and really focus on service for them - same as any client. This could mean recommending a competitor as a better option. It also means possibly investing time and effort, perhaps creating a demo of some possible solution that might help them decide. If there seems to be good trust building, maybe we should fly out to help them in a tricky time? If they regret the call with you in 6 months, something has gone wrong!

Many of the same activities in marketing & sales would be exactly the same activities we would do for a client. In every situation we scale our own personal investment to the trust and resources both sides are placing into the relationship. Almost all of the work is genuinely building a human relationship, letting them know we care, we want to help them, and here’s how. Sometimes, too, that means things naturally don’t work out, and that’s also OK. If this happens constantly, it’s a natural market signal we need to retool our niche and focus.

Eventually, you hope, a client signs a contract. Here, you run the risk of taking them for granted. Think of the situation I described earlier where I had to apologize to the CTO for shoddy work by my predecessor. The ‘apology’ I was engaging in – which included a ‘if we don’t shape up, you shouldn’t use us’ statement on my part – is not dissimilar from the kind of difficult ‘decision point’ a sales lead is at. Both require demonstrating our sincerity, showing the possible value we can/cannot have, and helping the client with their own decision making process.

If we’re not “continuing the sale” (in other words, really “valuing the relationship”) we’re dooming it. Like in personal life, both sides need to see what they’re getting, and it goes beyond just the delivery of working code to “can I count on this person in a pinch?” and “does this person genuinely care about me / my success?”

This focus on the relationship - where both sides invest trust and resources - is the key thing. Of course, a sales lead that drags us along and doesn’t invest anything on their end, shouldn’t be continued with. Same with a client that doesn’t pay a fair market value. They’re either just unable to invest the require resources or could just be taking advantage of us. However, when both sides (whether sales lead or client), show good faith and invest, you learn that consulting can be a virtuous cycle of trust, goodwill, and service. Your good clients will keep bringing you back. This is a great feeling!

Consulting as a Virtuous Cycle of Career Development

Another colleague of mine, Spencer Ingram, has described treating your career as a startup. And the full cycle I talk about above - from investing and advertising in marketable skills, to helping prospects decide whether your skills can help them, to ultimately helping clients - is a great feedback loop for your career. It’s like you’re constantly learning and interviewing for jobs. And when things dont work out at the “interview” you still are growing your network in your industry constantly.

This is one of the most compelling reason to go into consulting. You are constantly examining where your field is going and repositioning - all the while growing your network.

This happened to me all the time. Constantly I received signals from clients on areas of focus I should grow in my field. This led to many of my decisions, like creating the Elasticsearch Learning to Rank plugin. Learning to Rank is/was a hot topic, and Elasticsearch badly needed the functionality. The information I got from clients was this was a major need: so I made sure it was marketing land I was grabbing for OpenSource Connections. I knew our skills and capabilities needed to grow in this direction, and in so doing, we could address marketing/sales/client questions that kept cropping up.

The frustrations of consulting - why you might avoid it

Consulting is great. However, there’s always a rub. And as the years wore on, I found myself increasingly less excited by some of the rougher aspects of high-end technical consulting, ultimately making a switch to a different role:

Feast-or-famine sales cycles:

You have to gird yourself for a feast and famine reality. So you can tend to overdo it to make sure you have enough hour to bill. This means you can burn yourself out, trying to do what I just described in the sections above: trying to show too many clients you do truly care. You can easily overextend yourself worried that in 4 weeks you have no billable time. Then have it turn out you’ve oversold your time to clients. It can be hard to know when to take a vacation in this situation!

Rejection during sales:

There’s an emotional roller-coaster ride to first the excitement of the original call “BigName client has X hard problem” to the let down later on of “it turns out they found another vendor” or “we can’t work with these people cause of onerous contract language, and their lawyers won’t bend”. This feeds the feast-or-famine thinking. It’s also just a let-down: you were really excited about that problem! It seemed you and the client clicked! What went wrong? Often it’s things out of our control.

Becoming TOO attached to a solution or vision

One of the hardest things in consulting is that we’re really tourists. Our role isn’t really to deliver working code, per-se, in the same way as a normal, day-to-day technical. Often instead, our role is to help clients make decisions and educate them. It’s human to develop an attachment to one solution, vision, mindset, and to see it as TheWayForward:™: only to have politics, the latest reorg, etc, have the rug swept out from under you. And as you’re really a tourist in their org, not a native, so are unlikely to influence any new organizational direction.

Kept at arms length

Because you’re a tourist in the client’s org, you can tend to be kept at arms length. Often your impact is rather limited because of this. When you meet a new person at a client, the default perspective is to be seen as suspicious simply by having the label of ‘consultant’. You might not get to work on the cool problems when management would like their own people doing that work. You have to keep your attitude of service front and center, and not get too disappointed when the work changes to something less interesting, or goes in a direction you didn’t expect.

Clients Sometimes Hire “The Consultant” Because They’re Dysfunctional

I had a lot of fantastic clients. But there was occasionally a trend: many clients had some kind of organizational dysfunction they were unwilling to work through or unaware of. So instead they hired “the consultant” to fix the problem. You would arrive and realize they’re not succeeding more because Team A was siloed from Team B, or because manager Bob was not willing to invest what was needed, or a million other org reasons. Sometimes, with high levels of trust, clients would listen to your suggestions about these problems. Unfortunately, much of the time, they were actually aware and unwilling to solve the problem - problems which were out of your control and had little to do with the technical wizardry you were supposedly capable of solving. Sadly, in these cases you can become their needed scapegoat when you don’t solve the problem due to said org challenges.

Travel!

This one’s probably obvious. Earlier in my 30s, the jaunt over to Geneva or London to work with a client seemed romantic and exciting. But as my kids got older, even shorter trips became draining. You simply don’t sleep well in hotels and don’t do your best at the client. Not to mention getting there and back!

Should you become a consultant?

If you’ve taken on a job or two and are hungry for more, I encourage you to consider consulting. With an entrepreneurial spirit, you can grow your personal brand and technical skills. Even more important: developing trust with others and genuinely caring about helping will serve you regardless of where you ultimately end up.

If you want any career advice, don’t hesitate to reach out. I’m not always sure I’ll have time, but I’ll do my best :)

(And special thanks to my colleagues at OpenSource Connections, it truly is a special place to take on this kind of role! I can thoroughly recommend them as an employer ;) )

Special Thanks to John Berryman and Simon Eskildsen for reviewing this post and giving substantive edits and feedback!