***Managers: Many of you have questions on how to hire the best people without a recruiter's help. If that's you, read this:***

$100 product can change your life and your compan's trajectory.

I promise you this will be worth the 2-minute read.

Do you know what you NEED TO get out of each interview?

Hiring doesn't have to be hard, but it DOES have to be thoughtful.

Don't hire someone unless you are 100% on them. Get there by unlocking the POWER OF CHOICE and implementing easy, low-cost hacks to hire right.

By learning the tools of the recruiter, like how to source, you unlock the Power of Choice. Choice ultimately solves all of the hiring problems you will face during the first years of your company. You need to do some things that a recruiter does to unlock the Power of Choice.

I'm here to teach you - the hiring manager or founders or executive - the secrets to hiring and unlock the Power of Choice.

Building the right team is the biggest thing you will do as a manager. I'm here to give you a practical guide on how to do that when you don't have the luxury of a recruiter on staff.

Bootstrap Talent: Time Saving Guide to Hiring Right

Written for Operators, Managers, Founders, Executives and YOU

I wrote this because there isn't a definitive guide on how to hire written for the operator. Everything is inside-baseball recruiter talk. When Hiring managers don't have recruiting support, they need to execute on the minimal, most effective pieces to get hiring done right in as low time as possible.

Being the manager has its advantages. You can move fast, make decisions, and sell all in one unit. Recruiters can't do that. Advantage = You.

Recruiters spend their whole work day learning and improving how they hire, including how to best bring in talent and unlock the Power of Choice. Advantage = Recruiters. You can't afford to do that, so I distilled what they have learned into a simple guide focused on the stuff you can actually do in the time you have.

I wish I had this guide when I got my first big-kid job. Here is what I did wrong:

1. Didn't know what I was looking for. Wrote terrible job descriptions.
2. Other people on my team didn't know what I was hiring for. I wasted everyone's time.
3. I didn't know how to find the right people. I didn't have any pipeline, so I never unlocked the Power of Choice.
4. The great people I did meet, I didn't hire all of them. I failed to build the best team.
5. I didn't do reference checks. I paid for that months later when someone I hired didn't work out and I had to manage them out, which sucks.

That's just a sample! And I was a former recruiter. I knew what I was up against and I still made so many mistakes because I just didn't know how to recruit for my own team. I didn't have a guide to recruiting written for me, the operator. That's this guide.

Building a better team, makes you better. It's the key to success as a leader and a company.

That's the secret. I spoke with a big time VP of Engineering and I asked them what their secret was to being so successful at so many different high growth companies: Team. That was it. That's what separates player-coaches from true managers or leaders: Hiring. This individual spent 80%+ of their time hiring.  They were ruthless about it and took matters into their own hands even when there was a recruiting team. They spent a ton of time doing what was necessary. My goal is to get you those same results while continuing to execute. That's what you need to do and what I can give you.

If you hire the best team you can and things will become easier. I promise you that.But conversely, make some bad hires, and you are in micromanage and manage-out hell for weeks to months. That will kill your ability to execute and the overall output of your team.

Some managers never recover from a bad hire

Save time now by hiring the best people you can and avoid those people that just wont work out. The Power of Choice can eliminate hiring mistakes and bring in talent that you didn't know existed and that you didn't even know you needed.

There is a solution. Internal Recruiters have been plying this trade for 10 years now. There is a reason why every successful company has invested heavily in recruiting teams. That may not be you right now, and if thats the case, or if you want to just up your game as a hiring manager, Bootstrap Talent if your guide to the best team.

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Bootstrap saves you time on hiring the right talent.

Here's what I cover:

The Power of Choice: Great teams come from access and choice.

Laying the groundwork so you hire the right people: Mission, Vision and Values

The right tools at sub-scale: standing up your talent acquisition stack

Why you need to build a diverse team, and how

How to write the right job descriptions

How sourcing works, including how to negotiate with agencies, maximize inbound, leveraging marketing channels, and creating an effective referral program.

Boilerplate hiring process: An easy to implement and low time cost hiring process designed to get you hiring signal

How to close candidates

How to do due diligence: Reference checking and when to dig deeper

Bootstrap a simple onboarding process and unock the keys to employee happiness

How to hire your first recruiter

Why Bootstrap Talent?

Decision-making vs Execution: Whats the difference between being a contrarian and being misaligned?

The people in every organization I have been in have had some recalcitrance to saying what is on their mind - especially publicly.  Tools like TinyPulse and Lattice try to create ways to give feedback anonymously, and that is useful. All feedback is useful. But feedback is most useful when it is vocalized face to face.  Then a conversation can happen. The more people in your organization speaking their minds the better the decision making.

Why do people fear speaking their mind?

There is absolutely a power dynamic at play. That is something management needs to be good about acknowledging in order to create a transparent, risk-taking culture and I wont get into that in this post (though it is very important). Beyond that, and the crux of this post, is a misunderstanding of what the expectations are for folks in the decision-making phase vs the execution phase.

So why are some employees celebrated for being contrarian and others are seen as renegades? It comes down to when the employee is pushing back and then ultimately in how that manifests in their execution. Understanding when decisions are being made and when they have already been made (and it is now time to execute) is key to understanding the distinction.

Before going forward, I want to state, that differentiating decision making and execution is a skill and knowing how to be a persistent contrarian in decision-making processes is a super power. It is not necessarily intuitive. So while the concepts can seem easy, in practice they can be tricky to apply, but learning these skills is a must for management and other strategic roles.

Decision Making

First, let's talk decision making. Making decisions is very important, especially for small companies. In a small company, changing tack is pretty easy, but hesitation is deadly (as I blogged about a while ago in "Does your organization make decisions?"). In all organizations, decisions need to be made in order to move forward, but startups specifically need to make decisions more than they need to make the right decisions; if that makes sense.

Decisions can be big or small. Top to bottom or bottoms-up. They can be the color of a button or the purpose of your organization. All of these decisions need to be made, with the bigger the decision typically having a longer decision making cycle and often require more people to be involved.

As an employee, it is key to understand when the room is in a decision making phase. In this phase, it is incredibly valuable to be a voice of dissent, even as just a 'devil's advocate".  This input can help shape the decisions being made and help the organization make better decisions. This can be a super power for an employee and can quickly garner notice from the top of the organization and lead to promotions into management or other strategic roles.

Decisions need to be made. Decision-makers in a company are doing their best to make decisions with the data available to them. Often times these decisions are wrong.  It's important to keep prospective and know that the most important thing is that decisions are being made, communicated and executed on.


Without the right communication, nothing happens. The tricky thing about communication is that in the early days (when the organization is small) communicating decisions is pretty much free.  Decisions are made as a company, and context is easy to come by. As an organization grows, communication becomes more costly. It is not uncommon for decision-making to be the easy part and communicating the decision being the hard part (and requiring more time and effort to do well).

While working remotely, it makes sense to regularly document and share out decisions using Slack or email. Once you are back in an office, make sure to start putting rigor around communicating decisions whenever you add a layer of management.  Every layer of management will require additional effort to communicate decisions.


Once the decision is made, it is time to execute on that decision. With a lot of decisions being made, you will often need to "disagree and commit" which is an essential tool for any executive or strategic leader. Dissension is key in decision making but alignment in execution is 100% necessary for a functional organization. As organizations get larger it becomes more common than not for any given employee to be executing on decisions that they don't 100% agree with. That is okay and as organizations and remits grow, providing input into many decisions but deciding on few of them is to be expected.

When the organization is executing it is no longer productive to debate the decision that was already made. Down the road, once something has been tried, the decision-making window opens back up and a new path may be set, but while in the execution phase, not following through on the decision means that the decision was never attempted and the desired learning and output from that decision will be unlikely to materialize. With many folks in an organization, some executing and some not, the organization will flounder and eventually fail. This is the most common type of organizational dysfunction.

I want to note that within executive teams or leadership circles, it is not productive to harp on past decisions made by a colleague. Chronic poor decision making is noteworthy and should encourage exploration by leadership, but I want to caution against introducing conservative decision making or decision-making paralysis by persistently criticizing decisions already made. Disagree and commit means letting past decisions go and looking toward the present and future.

During the execution phase, the focus is on execution, driving alignment and learning.  Anyone in an organization can help in driving alignment. In organizations that have recently grown or where the team fabric is just being knit, there will be gaps in the communications of decisions. In this case, identifying these gaps, seeking answers and proactively sharing information on a decision will help drive alignment during the execution phase. This type of behavior is highly valuable. Also, while executing, think about feedback as objective reporting: Removing any priors, and focusing on dispassionate observation or "What am I witnessing right now?"  That will feed into future decision making.

Where relationships between employer and employee get fraught is in the Execution phase: A decision has been made, and for whatever reason, the individual is not able or willing to carryout that decision. Sometimes this is a failure to communicate, and assuming the best intentions of others is the best first course of action. But in cases where communication can be ruled out, then the individual is likely misaligned with the decision and by extension the organization. To an observer, this may appear as if their colleague is just voicing their dissent, but what is actually of concern is a lack of execution on a decision already made.

Many times, a failure to execute by an otherwise competent employee is a conscious or subconscious recognition that they no longer believe in what the organization is doing or the direction it is going in. To anyone experiencing this, that's okay! That happens all the time. If that's the case, talking through a way to exit is the best course of action for everyone involved.

Take Aways:
  1. If your organization isn't making decisions, thats a red flag.
  2. If there is a decision being made, speak freely.
  3. When a decision is made, execute your face off regardless of whether you think it was the right decision.
  4. Help drive alignment and provide observations (stated as facts) about what you are seeing during execution.
  5. Repeat 2-4.

Hope this helps! Bring on the dissent and then let's all get down to executing.

Who am I?

Trent Krupp

VP of Operations at Triplebyte. Founded an agency in my 20's, sold it to Hired and became employee 5. Recruited for Atomic (VC), Credit Sesame and MakerSights. Helped the founders of recruitment tech startups Shift.org, Terminal and Beacon in the early days.

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