Estimation and Meeting Sprint Commitments

In this episode of SoundNotes, Dave Prior and Derek Huether respond to a couple questions from students who have taken a LeadingAgile CSM and/or CSPO class over the past couple months. Here are the questions they will address in this short video podcast:

Question 1:

My team seems to have a problem with estimating and understanding the estimating concepts. The team members are accustomed to traditional waterfall projects and estimating everything in units of time. How can I help them understand estimating, but continue to complete the sprints with no PBIs (Product Backlog Items) rolling over to the next sprint?

Question 2:

I have a team lead who is skeptical of scrum, especially metrics related to the process. He doesn’t think carryover matters from sprint to sprint as long as we’re “creating value” and getting the program priorities completed. Any advice on how to convince him that metrics can be a tool for good, and that the sanctity of the sprint commitment matters?

8 Domains Executives should Plan and Coordinate

Planning and Coordinating use Agile PPM tools

Executives are responsible for maintaining the structure of the organization and supporting the mechanisms that enable the flow of value across many teams. To that, executives should plan and coordinate across major organizational domains. Though I believe there are eight domains which executives should be planning and coordinating in, I'm not prepared to say Sales & CRM or Marketing Management should be included in an Agile PPM tool (at this time). Beyond that, a single PPM tool should cover the remaining six domains.

Often, the first tools purchased are to help the delivery teams manage their daily work. As the organization evolves or grows, more tools are purchased to cover the gaps left by the team-level tools. The tools then become entrenched. At some point, organizations have a collection of tools they are trying to maintain and they lose sight of the original reasons for purchasing and implementing them.

Organizations then turn to PPM tools. There is a wide variety of motivations for using agile project portfolio management (PPM) tools. One key reason can simply be the desire for their teams to collaboratively plan. Other key reasons include the desire to prioritize and track work on a synchronized cadence, while providing visibility of the portfolio to the executive stakeholders. To meet organizational needs, the number of tools being used to satisfy these desires expand over time.

Before you choose an Agile PPM tool, remember that your company operations should influence how that tool is implemented across your organization, not the other way around.

What types of problems are Agile PPM tools good at solving?

Six Organizational Domains of Planning and Coordinating

Portfolio Management

The art and science of making decisions about investment mix and policy, matching investments to objectives and key results (OKRs), asset allocation for individuals and institutions, and balancing risk against performance. Your Agile PPM tool needs to provide a sufficient level of visibility of the roadmap and investment themes, through the lens of a portfolio team.

Program Management

The process of managing several related projects or products that are part of an investment portfolio. Your Agile PPM tool must provide a sufficient level of visibility of the release backlog and to allow for necessary elaboration for release targeting, all through the lens of a program or capability team.

Capacity Management

Deals with the organizations ability to create or develop new product. Capacity constraints in any process or resource can be a major bottleneck for a company. Your Agile PPM tool should make it easy to know what the organization and teams have historically delivered, in order to understand where the bottlenecks exist, and what to commit to in the future.

Human Capital Management

Related to people resource management. In order to deliver product predictably, it is necessary to have stable teams, providing specific competencies. Your organization needs the right people in place to deliver on commitments in the portfolio. Do you need to hire or replace people? Your Agile PPM tool should help facilitate a conversation around who are the right people, what teams they should be on, and when we need them on a team.

Dependency Management

The ability to either encapsulate or orchestrate around “dependent” organizational, structural, or technical activities. Dependencies tend to be a major productivity killer for organizations. They slow and sometimes stop the ability to deliver value. It is critical that your Agile PPM tool provides indications of dependencies across the organization. Having the first indication of a dependency discovered after a delivery team has already made a commitment against its impacted deliverable is too late.

Budget Management

Refers to a financial plan for a defined period of time. It may also include planned revenues, resource quantities, costs and expenses, assets, liabilities and cash flows. Your Agile PPM tool must provide the necessary information to shift conversations from just scope and schedule to budget.


Use the above list as a guide to catalog tools your organization is using (or considering) for planning and coordinating. Are there gaps or are there overlaps and duplications? If you have overlaps and duplications, there is an opportunity for you to consolidate some of those tools. Begin consolidating tools, and you may reclaim some budget next year you didn't think you had.

Want to know how you are covering the six or eight domains? Schedule an assessment with me.

Getting Clarity


I believe the number one reason for failure or waste is a lack of clarity or understanding. If you getting clarity on something, it gives you the freedom to decide if you want to do it or not.  If something is ambiguous, you may agree in principle but you don't know what you're really getting yourself into.


Firstly, what are your Objectives and Key Results (OKR)? How do you set and communicate goals and results in your organization? Because you want people to move together in the right direction, you need to get clarity.


What are your Key Performance Indicators (KPI)? How do you want to measure value that demonstrates how effectively your company is achieving key business objectives?  Because you want your organization to evaluate its success at reaching targets, you need to get clarity.


What does the team design or structure of the organization look like on portfolio, program, product, and service layers? We need a shared understanding of which individuals or teams are responsible for what.


What does the governance of the organization look like? How do we manage our budget, dependencies, risks, or quality? What are the inputs, outputs, and artifacts?

Metrics and Tools

Because we want to manage our system of delivery, what are necessary metrics and tools of the organization?

Getting Clarity

Remember, if you expect others to commit to something, regardless if it's a process or a deliverable, we need a shared understanding.

Review of the book Angel by Jason Calacanis

I just finished reading and listening to Angel: How to Invest in Technology Startups, a book by Jason Calacanis.  I first mentioned Jason on this blog back in 2009, when I wrote "starting is easy; finishing is hard." Fast forward 8 years.

First Thoughts

First, let me say, this is a great book. I'm now going back, highlighting sections, and ready to put what I have read to work. I also recommend downloading the Audible version. It's read by Jason and has some extras at the end (not in the physical book).

So many other books are all hype, promising everyone that they can do anything. They promise you fame and fortune, resulting in readers changing their profiles to read "Hustler, Grinder, and Lifestyle Coach". I love that Jason didn't say everyone can be an angel investor.

Actually, he did but there were some clear caveats. If you want to be an effective angel investor, you'll need a combination of things and Jason details what they are (see chapter 4).

Though you might not meet all of Jason's criteria to be an effective angel investor, I still think you should read (and listen to) this book if you're a founder or thinking of getting into angel investing.


  1. Jason was specific about what you need to do, to be an effective angel investor.  Right away, you'll realize if you can or can not do this.  Sorry to all of those precious snowflakes out there who think they can do anything.  If you don't have the money or stomach for high risk, you can't do this.
  2. At $1000-$2500 for each of your first 10 investments, if you don't have the money, you can't afford to be an angel investor.
  3. If you can't deploy even greater amounts of money, in the event one of your startups gets a Series A from a known venture capital firm, you'll get diluted. (do a search on Pro Rata)
  4. If you're unwilling to move to Silicon Valley, your deal flow may be limited. (I like my home in Maryland)
  5. You have less than a 1% chance of being successful. (The truth hurts)

I just exchanged Twitter DM's with Jason.  He wanted to note that he did talk about being an angel with no money (advisor shares!).  I want to make sure I properly represent the book so I'm adding this blog post edit.  Also, I plan to write other blog posts about the book.


  1. Jason was specific about what you need to do, to be an effective angel investor.  Right away, you'll realize if you can or can not do this.  Note I'm listing this as both a Pro and a Con.
  2. He describes probably the safest path you can take if you're going to get into angel investing.  Granted, you still have less than a 1% chance of being successful.
  3. Jason speaks and writes from the heart. He sounds like a kid from Brooklyn.  He actually reads the Audible version of his book.  I've been listening to him since the beginning of his This Week in Startups (TWIST) podcast. It was good to hear his voice and not some voice actor.
  4. He has an impressive track record in angel investing so he's not like these knuckleheads you see out there trying to be "lifestyle advisors".
  5. "You only have to be right once" ~Mark Cuban

Now, it's time to put in the work.


Disclaimer: I was in no way compensated for the writing of this review.