A practical playbook for founders and engineering managers to stop wasting time trying to get started with DevOps the right way
Is this article for you?
Maybe you're a CTO.
Maybe you're an engineering manager.
If you think about hiring you first DevOps Engineer - this article is for you.
It will save you 6 months of wasted mental capacity.
How? By dedicating 10 hours to planning.
I'll share with you here exactly what to do during those 10 hours.
You might know this story TOO well
~ "I need to focus on the product"
You are building your company’s product.
You start thinking about the development process and building or improving production.
Then, you read about DevOps somewhere and think to yourself: “This seems like what I need”.
~ "DevOps is expensive"
You start looking for a DevOps Engineer, but you find out the standard DevOps salary - “Oh, that’s pretty expensive for our budget”.
So you decide to wait. “Hiring a developer is more important right now” you tell yourself.
A month goes by, and you and your team are grinding away, building a kickass product.
But alas! The missing development automation hurts collaboration, the cloud infrastructure is a collection of manual changes - and you’re not sure if the system is built well.
So, you make a decision, and you post your first “DevOps Position”, congrats!
~ "I'll interview some candidates"
Candidates start streaming in, and you start interviewing.
After interviewing the 3rd candidate, you think to yourself “this is not it”.
Every candidate is missing a different piece of the required knowledge.
One doesn’t know AWS, the other isn’t familiar with "", and the last one only worked with on-prem before.
And so, you re-evaluate.
~ "I'll do it myself"
The realization is this: You can’t hire on knowledge for this position, you have to hire on skill and character.
BUT, you feel like the knowledge is crucial, at least at this point.
So you make another decision - I’ll invest some more time in this “DevOps” thing - I’ll learn.
You watch DevOps tutorials on Youtube.
You even subscribe to various DevOps Newsletters, something you didn’t do before.
Another month goes by.
~ "What do other startups do?"
After learning and implementing DevOps bits and pieces all over the place, it doesn’t feel right.
“Am I re-inventing the wheel and complicating the future?” you might ask yourself.
You take a step back, zoom-out, and ask other startup founders what they did at this stage.
That’s when you find out you’re not alone - “Oh! So it’s tough for other founders as well!”
But, each founder tells you something different.
One founder tells you to hire a freelancer - but that seems like just another hiring model and doesn’t solve the problem.
Another founder tells you to just hire a full-time DevOps Engineer - but your resources are limited, and you’d rather hire more developers to build the product.
Until one founder tells you to hire an agency: “Instead of a freelancer, get a company that’s built to get your DevOps right”.
~ "Maybe an agency?"
You’re convinced, and you start looking for agencies.
You get recommendations, you search online, and you start booking calls.
*1st call with a DevOps agency
*“Hi there! Yes we’re the solution for you! Let’s get started!”
2nd call with a DevOps agency
“Yes! We’ll provide you with a strong DevOps Engineer! Let’s get started!”
~ "I'll do it myself"
You choose not to go on the 3rd call and you pause the process.
Why? Because you realize: “These guys didn’t remove any uncertainty for me - how are they different from a freelancer?”
So you make another decision.
You’ll continue to do DevOps yourself, and maybe delegate some tasks to other team members.
That’s when you find out it was a trap! You got yourself into a loop!
~ "Oh no! it's a loop!"
After just one month you realize it’s not sustainable, and you repeat the same process:
- Open DevOps position
- Realize each candidate is missing something else
- Fear for the budget
- Stop the hiring
- Complete DevOps tasks yourself
- Consider a freelancer
- Drop the idea because it's similar hiring
- Consider an agency
- Interview a bunch of agencies
- No extra certainty or confidence from an agency
- Do DevOps work yourself
- Repeat
This loop is sometimes 2 months long, and sometimes 12 months long.
Either way, it slows down your company!
It occupies your thoughts.
It takes valuable time from you.
It speeds up global warming.
Maybe the global warming part was an exaggeration.
It’s amazing how many founders went through this exact same process.
Break the loop
I’m here to tell you:
- You can break the DevOps hiring loop
- You can promote DevOps efforts quickly AND accurately
- You can save 6-12 months of stumbling around
You need just 10 hours with a DevOps Expert
You need just 10 hours with a DevOps expert.
What you need most is perspective from an experienced individual.
You don’t yet have the DevOps perspective or experience? No problem.
Get a DevOps Expert to consult you on a hourly basis.
I call it "The 10 Hours DevOps Pill" 💊
Requirements for the DevOps expert
Not anyone will fit as your trusted DevOps expert.
Use someone that answers these criteria:
- Helped 10+ companies with DevOps - Has a wide perspective
- Consulted CTOs and VPs of R&D before - Understands the weight of culture in adopting DevOps
- Consulted DevOps Group and Team Leaders before - Understands how to manage the work
- Did lots of DevOps hands-on work before - Understands how to do the work
- You understand them - They know where you stand and have simple explanations. (Run away from the buzzwords throwers)
Spoiler: The contents of the 10 hours
- 2h - Share everything about your startup
- 2h - Ask what’s possible + What others did
- 2h - Set DevOps goals
- 2h - Choose a strategy
- 2h - Create a DevOps roadmap Let’s dive into the playbook for each meeting!
1st + 2nd Consultation Hours: Share, share, share
Share the state of your company with the DevOps expert.
Share your infrastructure, your code, your work process, everything!
Don’t be shy, and don’t justify - simply explain your startup’s goals and your reasoning.
(Sign an NDA first, of course)
3rd + 4th Consultation Hours: Understand what’s possible + Gain perspective
Take notes or record this call!
Ask the DevOps expert: What’s possible?
- How fast can changes reach production?
- How fast can you create new environments?
- How easily can your developers collaborate?
- How confidently can you change the system?
- What uptime can the system have?
- How aware can your team be of the system’s state?
Ask the DevOps expert: What did other startups do at this stage?
- What goals did they have?
- What DevOps efforts did they promote?
- Why did they decide those DevOps efforts?
- Which startups performed best? Why?
- Are there industry-unique considerations?
5th + 6th Consultation Hours: Set DevOps goals
You now know what’s possible, and what other companies do.
Time to set short-term, mid-term, and long term goals.
If you want to dive deep into useful DevOps principles, check out the CTO DevOps Handbook here 👈🏼.
7th + 8th Consultation Hours: Strategize
Based on your goals, strengths, and restrictions, choose a strategy.
Discuss the following options with your DevOps expert.
Possible Strengths
- Developers with DevOps background
- High budget
- Available time to manage the DevOps efforts
Possible Restrictions
- No budget
- Low budget
- DevOps needs are temporary for now
- No time to manage the DevOps efforts
| DevOps Engineer | Freelancer | Agency | Winner | |
|---|---|---|---|---|
| Budget | High | Medium | Medium | Freelancer / Agency |
| Management Effort Required | High | High | Low-Medium | Agency |
| Hourly Flexibility | Low | Medium | High | Agency |
| Ease of bridging knowledge gaps | Low-Medium | Low-Medium | Medium-High | Agency |
| Ease of building trust | High | Medium-High | Low-Medium | DevOps Engineer |
The available strategies
Hire a DevOps Engineer, Boost with the DevOps expert
- Create a DevOps roadmap with the DevOps Expert before hiring
- Get the DevOps expert to interview the candidates
- Get advice from the DevOps expert on what to examine during your interview with the candidates
- Prioritize the DevOps efforts with the DevOps Expert
- Plan the onboarding of the DevOps Engineer with the 6. DevOps expert
- Hire the DevOps Engineer
- Get advice on managing DevOps projects from the DevOps expert
- Discuss the DevOps tasks implementation with the DevOps Engineer and DevOps expert
- Occasionally or routinely consult with the DevOps expert on priorities, management, and engineering
Hire a DevOps freelancer, Boost with the DevOps expert
- Exactly as the above strategy
- Take advantage of the hourly flexibility when needed
Hire a DevOps agency, Boost with the DevOps expert
- Create a DevOps roadmap with the DevOps Expert before choosing an agency
- Share your requirements with the agency
- Filter out any agency that doesn’t provide you with a plan BEFORE work starts
- Get the plan reviewed by your DevOps expert: Does it make sense? Is the planned result desired?
- Make sure the DevOps agency’s ability to provide support after the work is done
- Asses the level of the DevOps agency’s DevOps Engineers with the help of the DevOps expert
- Make sure the DevOps agency is flexible with its hourly capacity
- Occasionally or routinely consult with the DevOps expert on priorities, management, and engineering
Advantages and disadvantages of the strategies
| Option | Good when | Bad when |
|---|---|---|
| Full-time + Expert | - Your budget is high - You need flexible DevOps capacity - Your team has DevOps background | - Your budget is low |
| Freelancer + Expert | - Your budget is low - You need flexible DevOps capacity - You can't risk losing DevOps capacity short-mid-term | |
| Agency + Expert | - Your budget is low - You need flexible DevOps capacity - You want an accurate plan before work starts - You frequently need to support new tools and technologies | - The agency doesn’t have flexible plans - The agency’s team isn’t experienced - The agency doesn’t create clarity before work starts |
9th + 10th Consultation Hours: Create a DevOps roadmap + Execute your strategy
You’re ready to create a DevOps roadmap and start executing your strategy!
Creating a DevOps roadmap is the first step of each of the strategies described above.
You had to do a bunch of things first:
- You needed a DevOps expert to help you break the vicious DevOps loop - Done.
- You needed to set DevOps goals rooted in a deep DevOps understanding and perspective - Done.
- You needed to get familiar with different strategies and choose the best one for you - Done!
You’re left with 2 things to do:
1 - Create the DevOps roadmap based on the goals and strategy you’ve set
2 - Start executing the strategy:
- Share the DevOps goals with the team
- Schedule the interviews with the Engineers/Freelancers/Agencies
- Use the DevOps expert to stay on track
- Set the milestones for the DevOps goals
- Create the tasks
- Complete the tasks
Prepare before starting the process
You want to do two things before jumping into the 10 hours:
- Before the first 2 hours: Perfect your DevOps terminology (will support rich discussions)
- Before the last 2 hours: List existing efforts that might slow down the DevOps roadmap (will help prioritizing)
Ask me anything
If you’re thinking about taking this “10-hours DevOps Pill”, feel free to reach out here.
Do it yourself
You now know the general process for breaking the DevOps loop.
You don’t NEED a DevOps expert.
Feel free to subscribe to my Newsletter and learn how to do it yourself here 👈🏼
Top comments (12)
Makes perfect sense
Thank you Arthur!
This is gold, and I'm not even a CTO or Engineering Manager.
Thank you for the feedback!
What’s your role? :)
"Regular" software engineer :)
wow
Thank you
Makes Sense
Thank you!
"Hiring DevOps" (or DevSecOps, if you will) has never made much sense to me. I tried to focus instead on hiring "cloud engineers" who had worked with multiple providers and could demonstrate experience with shared / agnostic technologies like Docker, Terraform, and Kubernetes. But honestly it appears to be too little too late--the labor market has spoken, and decided that Dev(Sec)Ops is actually a job title. Sigh.
I think you’re making a valid point.
I use the term DevOps Engineer because it’s what’s familiar, and to be most precise I’d use the term Platform Engineer.
It’s similar to how “astrology” took the good name from “astronomy”.